The substituent effect on the antioxidant capacity of catechols and resorcinols

Abstract The antioxidant capacity of polyphenols is widely recognized; especially, the catechol moiety is considered a key piece in the structure of natural compounds with this characteristic. The resorcinol is also a dihydroxybenzene that is present in natural antioxidants; however, fewer experimental and theoretical studies have been addressed to this moiety. This work reports a comparative study of the substituent effect on properties related to the antioxidant capacity, as energy ionization (I), and O–H bond dissociation enthalpy (BDE), to analyze the electron transfer and hydrogen atom transfer (HAT) mechanisms, in derivatives of phenols, catechols and resorcinols. In the set of substituents tested %$({-}\hbox {CH}_3, {-}\hbox {CH}_2\hbox {CH}_3, {-}(\hbox {CH}_2)_2{-}\hbox {CH}_3, {-}\hbox {CH}{=}\hbox {CH}_2, {-}\hbox {CH}{=}\hbox {CHCOOH}, {-}\hbox {COOH}%$ and %${-}\hbox {CO}(\hbox {CH}_2)_4{-}\hbox {CH}_3)%$ electron-withdrawing and electron-donating groups, including alkyl chains, are considered. We found that electron-donating substituents reduce I and O–H BDE of resorcinols and catechols derivatives. In addition, the length of the alkyl chains is not relevant on resorcinols neither on catechols. With regard to the HAT process, a double bond in a substituent favors it, while the –COOH group shows a contrary effect. The combination of a double bond with a –COOH group, in the substituent, increases the BDE and reduces the electron donor capacity, and this result suggests that this combination induces a reduction in the antioxidant capacity in one polyphenol compound. In several reports, an intramolecular hydrogen bond has been proposed within to the most stable structure of catechol. However, by using arguments from the atoms in molecules approach and the electron localization function, we show that such an interaction is not relevant to stabilize this conformation and consequently and this is the reason that explains the unimportance of this interaction in the properties studied here and in previous studies. Ausführliche Beschreibung

Gespeichert in:

Autor*in:	Ortega-Moo, Cristina [verfasserIn] Garza, Jorge Vargas, Rubicelia

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2016

Schlagwörter:	Antioxidant capacity Ionization energy Bond dissociation energy Resorcinol and catechol derivatives Hydrogen bond

Anmerkung:	© Springer-Verlag Berlin Heidelberg 2016

Übergeordnetes Werk:	Enthalten in: Theoretical chemistry accounts - Berlin : Springer, 1962, 135(2016), 7 vom: 05. Juli
Übergeordnetes Werk:	volume:135 ; year:2016 ; number:7 ; day:05 ; month:07

Links:	Volltext

DOI / URN:	10.1007/s00214-016-1932-7

Katalog-ID:	SPR002075334

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100	1		\|a Ortega-Moo, Cristina \|e verfasserin \|4 aut
245	1	4	\|a The substituent effect on the antioxidant capacity of catechols and resorcinols
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520			\|a Abstract The antioxidant capacity of polyphenols is widely recognized; especially, the catechol moiety is considered a key piece in the structure of natural compounds with this characteristic. The resorcinol is also a dihydroxybenzene that is present in natural antioxidants; however, fewer experimental and theoretical studies have been addressed to this moiety. This work reports a comparative study of the substituent effect on properties related to the antioxidant capacity, as energy ionization (I), and O–H bond dissociation enthalpy (BDE), to analyze the electron transfer and hydrogen atom transfer (HAT) mechanisms, in derivatives of phenols, catechols and resorcinols. In the set of substituents tested %$({-}\hbox {CH}_3, {-}\hbox {CH}_2\hbox {CH}_3, {-}(\hbox {CH}_2)_2{-}\hbox {CH}_3, {-}\hbox {CH}{=}\hbox {CH}_2, {-}\hbox {CH}{=}\hbox {CHCOOH}, {-}\hbox {COOH}%$ and %${-}\hbox {CO}(\hbox {CH}_2)_4{-}\hbox {CH}_3)%$ electron-withdrawing and electron-donating groups, including alkyl chains, are considered. We found that electron-donating substituents reduce I and O–H BDE of resorcinols and catechols derivatives. In addition, the length of the alkyl chains is not relevant on resorcinols neither on catechols. With regard to the HAT process, a double bond in a substituent favors it, while the –COOH group shows a contrary effect. The combination of a double bond with a –COOH group, in the substituent, increases the BDE and reduces the electron donor capacity, and this result suggests that this combination induces a reduction in the antioxidant capacity in one polyphenol compound. In several reports, an intramolecular hydrogen bond has been proposed within to the most stable structure of catechol. However, by using arguments from the atoms in molecules approach and the electron localization function, we show that such an interaction is not relevant to stabilize this conformation and consequently and this is the reason that explains the unimportance of this interaction in the properties studied here and in previous studies.
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700	1		\|a Garza, Jorge \|4 aut
700	1		\|a Vargas, Rubicelia \|0 (orcid)0000-0003-0180-5727 \|4 aut
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912			\|a GBV_ILN_65
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912			\|a GBV_ILN_70
912			\|a GBV_ILN_73
912			\|a GBV_ILN_74
912			\|a GBV_ILN_90
912			\|a GBV_ILN_95
912			\|a GBV_ILN_100
912			\|a GBV_ILN_101
912			\|a GBV_ILN_105
912			\|a GBV_ILN_110
912			\|a GBV_ILN_120
912			\|a GBV_ILN_138
912			\|a GBV_ILN_150
912			\|a GBV_ILN_151
912			\|a GBV_ILN_152
912			\|a GBV_ILN_161
912			\|a GBV_ILN_170
912			\|a GBV_ILN_171
912			\|a GBV_ILN_187
912			\|a GBV_ILN_206
912			\|a GBV_ILN_213
912			\|a GBV_ILN_224
912			\|a GBV_ILN_230
912			\|a GBV_ILN_250
912			\|a GBV_ILN_267
912			\|a GBV_ILN_281
912			\|a GBV_ILN_285
912			\|a GBV_ILN_293
912			\|a GBV_ILN_370
912			\|a GBV_ILN_602
912			\|a GBV_ILN_636
912			\|a GBV_ILN_702
912			\|a GBV_ILN_2001
912			\|a GBV_ILN_2003
912			\|a GBV_ILN_2004
912			\|a GBV_ILN_2005
912			\|a GBV_ILN_2006
912			\|a GBV_ILN_2007
912			\|a GBV_ILN_2008
912			\|a GBV_ILN_2009
912			\|a GBV_ILN_2010
912			\|a GBV_ILN_2011
912			\|a GBV_ILN_2014
912			\|a GBV_ILN_2015
912			\|a GBV_ILN_2020
912			\|a GBV_ILN_2021
912			\|a GBV_ILN_2025
912			\|a GBV_ILN_2026
912			\|a GBV_ILN_2027
912			\|a GBV_ILN_2031
912			\|a GBV_ILN_2034
912			\|a GBV_ILN_2037
912			\|a GBV_ILN_2038
912			\|a GBV_ILN_2039
912			\|a GBV_ILN_2044
912			\|a GBV_ILN_2048
912			\|a GBV_ILN_2049
912			\|a GBV_ILN_2050
912			\|a GBV_ILN_2055
912			\|a GBV_ILN_2056
912			\|a GBV_ILN_2057
912			\|a GBV_ILN_2059
912			\|a GBV_ILN_2061
912			\|a GBV_ILN_2064
912			\|a GBV_ILN_2065
912			\|a GBV_ILN_2068
912			\|a GBV_ILN_2070
912			\|a GBV_ILN_2086
912			\|a GBV_ILN_2088
912			\|a GBV_ILN_2093
912			\|a GBV_ILN_2106
912			\|a GBV_ILN_2107
912			\|a GBV_ILN_2108
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912			\|a GBV_ILN_2111
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912			\|a GBV_ILN_2116
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912			\|a GBV_ILN_2119
912			\|a GBV_ILN_2122
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912			\|a GBV_ILN_2188
912			\|a GBV_ILN_2190
912			\|a GBV_ILN_2232
912			\|a GBV_ILN_2336
912			\|a GBV_ILN_2446
912			\|a GBV_ILN_2470
912			\|a GBV_ILN_2472
912			\|a GBV_ILN_2507
912			\|a GBV_ILN_2522
912			\|a GBV_ILN_2548
912			\|a GBV_ILN_4035
912			\|a GBV_ILN_4037
912			\|a GBV_ILN_4046
912			\|a GBV_ILN_4112
912			\|a GBV_ILN_4125
912			\|a GBV_ILN_4242
912			\|a GBV_ILN_4246
912			\|a GBV_ILN_4249
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912			\|a GBV_ILN_4305
912			\|a GBV_ILN_4306
912			\|a GBV_ILN_4307
912			\|a GBV_ILN_4313
912			\|a GBV_ILN_4322
912			\|a GBV_ILN_4323
912			\|a GBV_ILN_4324
912			\|a GBV_ILN_4325
912			\|a GBV_ILN_4326
912			\|a GBV_ILN_4333
912			\|a GBV_ILN_4334
912			\|a GBV_ILN_4335
912			\|a GBV_ILN_4336
912			\|a GBV_ILN_4338
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Indexfelder

author_variant	c o m com j g jg r v rv
matchkey_str	article:14322234:2016----::hsbttetfetnhatoiataaiyfae
hierarchy_sort_str	2016
publishDate	2016
allfields	10.1007/s00214-016-1932-7 doi (DE-627)SPR002075334 (SPR)s00214-016-1932-7-e DE-627 ger DE-627 rakwb eng Ortega-Moo, Cristina verfasserin aut The substituent effect on the antioxidant capacity of catechols and resorcinols 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer-Verlag Berlin Heidelberg 2016 Abstract The antioxidant capacity of polyphenols is widely recognized; especially, the catechol moiety is considered a key piece in the structure of natural compounds with this characteristic. The resorcinol is also a dihydroxybenzene that is present in natural antioxidants; however, fewer experimental and theoretical studies have been addressed to this moiety. This work reports a comparative study of the substituent effect on properties related to the antioxidant capacity, as energy ionization (I), and O–H bond dissociation enthalpy (BDE), to analyze the electron transfer and hydrogen atom transfer (HAT) mechanisms, in derivatives of phenols, catechols and resorcinols. In the set of substituents tested %$({-}\hbox {CH}_3, {-}\hbox {CH}_2\hbox {CH}_3, {-}(\hbox {CH}_2)_2{-}\hbox {CH}_3, {-}\hbox {CH}{=}\hbox {CH}_2, {-}\hbox {CH}{=}\hbox {CHCOOH}, {-}\hbox {COOH}%$ and %${-}\hbox {CO}(\hbox {CH}_2)_4{-}\hbox {CH}_3)%$ electron-withdrawing and electron-donating groups, including alkyl chains, are considered. We found that electron-donating substituents reduce I and O–H BDE of resorcinols and catechols derivatives. In addition, the length of the alkyl chains is not relevant on resorcinols neither on catechols. With regard to the HAT process, a double bond in a substituent favors it, while the –COOH group shows a contrary effect. The combination of a double bond with a –COOH group, in the substituent, increases the BDE and reduces the electron donor capacity, and this result suggests that this combination induces a reduction in the antioxidant capacity in one polyphenol compound. In several reports, an intramolecular hydrogen bond has been proposed within to the most stable structure of catechol. However, by using arguments from the atoms in molecules approach and the electron localization function, we show that such an interaction is not relevant to stabilize this conformation and consequently and this is the reason that explains the unimportance of this interaction in the properties studied here and in previous studies. Antioxidant capacity (dpeaa)DE-He213 Ionization energy (dpeaa)DE-He213 Bond dissociation energy (dpeaa)DE-He213 Resorcinol and catechol derivatives (dpeaa)DE-He213 Hydrogen bond (dpeaa)DE-He213 Garza, Jorge aut Vargas, Rubicelia (orcid)0000-0003-0180-5727 aut Enthalten in Theoretical chemistry accounts Berlin : Springer, 1962 135(2016), 7 vom: 05. Juli (DE-627)25490971X (DE-600)1463180-5 1432-2234 nnns volume:135 year:2016 number:7 day:05 month:07 https://dx.doi.org/10.1007/s00214-016-1932-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 135 2016 7 05 07
spelling	10.1007/s00214-016-1932-7 doi (DE-627)SPR002075334 (SPR)s00214-016-1932-7-e DE-627 ger DE-627 rakwb eng Ortega-Moo, Cristina verfasserin aut The substituent effect on the antioxidant capacity of catechols and resorcinols 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer-Verlag Berlin Heidelberg 2016 Abstract The antioxidant capacity of polyphenols is widely recognized; especially, the catechol moiety is considered a key piece in the structure of natural compounds with this characteristic. The resorcinol is also a dihydroxybenzene that is present in natural antioxidants; however, fewer experimental and theoretical studies have been addressed to this moiety. This work reports a comparative study of the substituent effect on properties related to the antioxidant capacity, as energy ionization (I), and O–H bond dissociation enthalpy (BDE), to analyze the electron transfer and hydrogen atom transfer (HAT) mechanisms, in derivatives of phenols, catechols and resorcinols. In the set of substituents tested %$({-}\hbox {CH}_3, {-}\hbox {CH}_2\hbox {CH}_3, {-}(\hbox {CH}_2)_2{-}\hbox {CH}_3, {-}\hbox {CH}{=}\hbox {CH}_2, {-}\hbox {CH}{=}\hbox {CHCOOH}, {-}\hbox {COOH}%$ and %${-}\hbox {CO}(\hbox {CH}_2)_4{-}\hbox {CH}_3)%$ electron-withdrawing and electron-donating groups, including alkyl chains, are considered. We found that electron-donating substituents reduce I and O–H BDE of resorcinols and catechols derivatives. In addition, the length of the alkyl chains is not relevant on resorcinols neither on catechols. With regard to the HAT process, a double bond in a substituent favors it, while the –COOH group shows a contrary effect. The combination of a double bond with a –COOH group, in the substituent, increases the BDE and reduces the electron donor capacity, and this result suggests that this combination induces a reduction in the antioxidant capacity in one polyphenol compound. In several reports, an intramolecular hydrogen bond has been proposed within to the most stable structure of catechol. However, by using arguments from the atoms in molecules approach and the electron localization function, we show that such an interaction is not relevant to stabilize this conformation and consequently and this is the reason that explains the unimportance of this interaction in the properties studied here and in previous studies. Antioxidant capacity (dpeaa)DE-He213 Ionization energy (dpeaa)DE-He213 Bond dissociation energy (dpeaa)DE-He213 Resorcinol and catechol derivatives (dpeaa)DE-He213 Hydrogen bond (dpeaa)DE-He213 Garza, Jorge aut Vargas, Rubicelia (orcid)0000-0003-0180-5727 aut Enthalten in Theoretical chemistry accounts Berlin : Springer, 1962 135(2016), 7 vom: 05. Juli (DE-627)25490971X (DE-600)1463180-5 1432-2234 nnns volume:135 year:2016 number:7 day:05 month:07 https://dx.doi.org/10.1007/s00214-016-1932-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 135 2016 7 05 07
allfields_unstemmed	10.1007/s00214-016-1932-7 doi (DE-627)SPR002075334 (SPR)s00214-016-1932-7-e DE-627 ger DE-627 rakwb eng Ortega-Moo, Cristina verfasserin aut The substituent effect on the antioxidant capacity of catechols and resorcinols 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer-Verlag Berlin Heidelberg 2016 Abstract The antioxidant capacity of polyphenols is widely recognized; especially, the catechol moiety is considered a key piece in the structure of natural compounds with this characteristic. The resorcinol is also a dihydroxybenzene that is present in natural antioxidants; however, fewer experimental and theoretical studies have been addressed to this moiety. This work reports a comparative study of the substituent effect on properties related to the antioxidant capacity, as energy ionization (I), and O–H bond dissociation enthalpy (BDE), to analyze the electron transfer and hydrogen atom transfer (HAT) mechanisms, in derivatives of phenols, catechols and resorcinols. In the set of substituents tested %$({-}\hbox {CH}_3, {-}\hbox {CH}_2\hbox {CH}_3, {-}(\hbox {CH}_2)_2{-}\hbox {CH}_3, {-}\hbox {CH}{=}\hbox {CH}_2, {-}\hbox {CH}{=}\hbox {CHCOOH}, {-}\hbox {COOH}%$ and %${-}\hbox {CO}(\hbox {CH}_2)_4{-}\hbox {CH}_3)%$ electron-withdrawing and electron-donating groups, including alkyl chains, are considered. We found that electron-donating substituents reduce I and O–H BDE of resorcinols and catechols derivatives. In addition, the length of the alkyl chains is not relevant on resorcinols neither on catechols. With regard to the HAT process, a double bond in a substituent favors it, while the –COOH group shows a contrary effect. The combination of a double bond with a –COOH group, in the substituent, increases the BDE and reduces the electron donor capacity, and this result suggests that this combination induces a reduction in the antioxidant capacity in one polyphenol compound. In several reports, an intramolecular hydrogen bond has been proposed within to the most stable structure of catechol. However, by using arguments from the atoms in molecules approach and the electron localization function, we show that such an interaction is not relevant to stabilize this conformation and consequently and this is the reason that explains the unimportance of this interaction in the properties studied here and in previous studies. Antioxidant capacity (dpeaa)DE-He213 Ionization energy (dpeaa)DE-He213 Bond dissociation energy (dpeaa)DE-He213 Resorcinol and catechol derivatives (dpeaa)DE-He213 Hydrogen bond (dpeaa)DE-He213 Garza, Jorge aut Vargas, Rubicelia (orcid)0000-0003-0180-5727 aut Enthalten in Theoretical chemistry accounts Berlin : Springer, 1962 135(2016), 7 vom: 05. Juli (DE-627)25490971X (DE-600)1463180-5 1432-2234 nnns volume:135 year:2016 number:7 day:05 month:07 https://dx.doi.org/10.1007/s00214-016-1932-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 135 2016 7 05 07
allfieldsGer	10.1007/s00214-016-1932-7 doi (DE-627)SPR002075334 (SPR)s00214-016-1932-7-e DE-627 ger DE-627 rakwb eng Ortega-Moo, Cristina verfasserin aut The substituent effect on the antioxidant capacity of catechols and resorcinols 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer-Verlag Berlin Heidelberg 2016 Abstract The antioxidant capacity of polyphenols is widely recognized; especially, the catechol moiety is considered a key piece in the structure of natural compounds with this characteristic. The resorcinol is also a dihydroxybenzene that is present in natural antioxidants; however, fewer experimental and theoretical studies have been addressed to this moiety. This work reports a comparative study of the substituent effect on properties related to the antioxidant capacity, as energy ionization (I), and O–H bond dissociation enthalpy (BDE), to analyze the electron transfer and hydrogen atom transfer (HAT) mechanisms, in derivatives of phenols, catechols and resorcinols. In the set of substituents tested %$({-}\hbox {CH}_3, {-}\hbox {CH}_2\hbox {CH}_3, {-}(\hbox {CH}_2)_2{-}\hbox {CH}_3, {-}\hbox {CH}{=}\hbox {CH}_2, {-}\hbox {CH}{=}\hbox {CHCOOH}, {-}\hbox {COOH}%$ and %${-}\hbox {CO}(\hbox {CH}_2)_4{-}\hbox {CH}_3)%$ electron-withdrawing and electron-donating groups, including alkyl chains, are considered. We found that electron-donating substituents reduce I and O–H BDE of resorcinols and catechols derivatives. In addition, the length of the alkyl chains is not relevant on resorcinols neither on catechols. With regard to the HAT process, a double bond in a substituent favors it, while the –COOH group shows a contrary effect. The combination of a double bond with a –COOH group, in the substituent, increases the BDE and reduces the electron donor capacity, and this result suggests that this combination induces a reduction in the antioxidant capacity in one polyphenol compound. In several reports, an intramolecular hydrogen bond has been proposed within to the most stable structure of catechol. However, by using arguments from the atoms in molecules approach and the electron localization function, we show that such an interaction is not relevant to stabilize this conformation and consequently and this is the reason that explains the unimportance of this interaction in the properties studied here and in previous studies. Antioxidant capacity (dpeaa)DE-He213 Ionization energy (dpeaa)DE-He213 Bond dissociation energy (dpeaa)DE-He213 Resorcinol and catechol derivatives (dpeaa)DE-He213 Hydrogen bond (dpeaa)DE-He213 Garza, Jorge aut Vargas, Rubicelia (orcid)0000-0003-0180-5727 aut Enthalten in Theoretical chemistry accounts Berlin : Springer, 1962 135(2016), 7 vom: 05. Juli (DE-627)25490971X (DE-600)1463180-5 1432-2234 nnns volume:135 year:2016 number:7 day:05 month:07 https://dx.doi.org/10.1007/s00214-016-1932-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 135 2016 7 05 07
allfieldsSound	10.1007/s00214-016-1932-7 doi (DE-627)SPR002075334 (SPR)s00214-016-1932-7-e DE-627 ger DE-627 rakwb eng Ortega-Moo, Cristina verfasserin aut The substituent effect on the antioxidant capacity of catechols and resorcinols 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Springer-Verlag Berlin Heidelberg 2016 Abstract The antioxidant capacity of polyphenols is widely recognized; especially, the catechol moiety is considered a key piece in the structure of natural compounds with this characteristic. The resorcinol is also a dihydroxybenzene that is present in natural antioxidants; however, fewer experimental and theoretical studies have been addressed to this moiety. This work reports a comparative study of the substituent effect on properties related to the antioxidant capacity, as energy ionization (I), and O–H bond dissociation enthalpy (BDE), to analyze the electron transfer and hydrogen atom transfer (HAT) mechanisms, in derivatives of phenols, catechols and resorcinols. In the set of substituents tested %$({-}\hbox {CH}_3, {-}\hbox {CH}_2\hbox {CH}_3, {-}(\hbox {CH}_2)_2{-}\hbox {CH}_3, {-}\hbox {CH}{=}\hbox {CH}_2, {-}\hbox {CH}{=}\hbox {CHCOOH}, {-}\hbox {COOH}%$ and %${-}\hbox {CO}(\hbox {CH}_2)_4{-}\hbox {CH}_3)%$ electron-withdrawing and electron-donating groups, including alkyl chains, are considered. We found that electron-donating substituents reduce I and O–H BDE of resorcinols and catechols derivatives. In addition, the length of the alkyl chains is not relevant on resorcinols neither on catechols. With regard to the HAT process, a double bond in a substituent favors it, while the –COOH group shows a contrary effect. The combination of a double bond with a –COOH group, in the substituent, increases the BDE and reduces the electron donor capacity, and this result suggests that this combination induces a reduction in the antioxidant capacity in one polyphenol compound. In several reports, an intramolecular hydrogen bond has been proposed within to the most stable structure of catechol. However, by using arguments from the atoms in molecules approach and the electron localization function, we show that such an interaction is not relevant to stabilize this conformation and consequently and this is the reason that explains the unimportance of this interaction in the properties studied here and in previous studies. Antioxidant capacity (dpeaa)DE-He213 Ionization energy (dpeaa)DE-He213 Bond dissociation energy (dpeaa)DE-He213 Resorcinol and catechol derivatives (dpeaa)DE-He213 Hydrogen bond (dpeaa)DE-He213 Garza, Jorge aut Vargas, Rubicelia (orcid)0000-0003-0180-5727 aut Enthalten in Theoretical chemistry accounts Berlin : Springer, 1962 135(2016), 7 vom: 05. Juli (DE-627)25490971X (DE-600)1463180-5 1432-2234 nnns volume:135 year:2016 number:7 day:05 month:07 https://dx.doi.org/10.1007/s00214-016-1932-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 135 2016 7 05 07
language	English
source	Enthalten in Theoretical chemistry accounts 135(2016), 7 vom: 05. Juli volume:135 year:2016 number:7 day:05 month:07
sourceStr	Enthalten in Theoretical chemistry accounts 135(2016), 7 vom: 05. Juli volume:135 year:2016 number:7 day:05 month:07
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	Antioxidant capacity Ionization energy Bond dissociation energy Resorcinol and catechol derivatives Hydrogen bond
isfreeaccess_bool	false
container_title	Theoretical chemistry accounts
authorswithroles_txt_mv	Ortega-Moo, Cristina @@aut@@ Garza, Jorge @@aut@@ Vargas, Rubicelia @@aut@@
publishDateDaySort_date	2016-07-05T00:00:00Z
hierarchy_top_id	25490971X
id	SPR002075334
language_de	englisch
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author	Ortega-Moo, Cristina
spellingShingle	Ortega-Moo, Cristina misc Antioxidant capacity misc Ionization energy misc Bond dissociation energy misc Resorcinol and catechol derivatives misc Hydrogen bond The substituent effect on the antioxidant capacity of catechols and resorcinols
authorStr	Ortega-Moo, Cristina
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issn	1432-2234
topic_title	The substituent effect on the antioxidant capacity of catechols and resorcinols Antioxidant capacity (dpeaa)DE-He213 Ionization energy (dpeaa)DE-He213 Bond dissociation energy (dpeaa)DE-He213 Resorcinol and catechol derivatives (dpeaa)DE-He213 Hydrogen bond (dpeaa)DE-He213
topic	misc Antioxidant capacity misc Ionization energy misc Bond dissociation energy misc Resorcinol and catechol derivatives misc Hydrogen bond
topic_unstemmed	misc Antioxidant capacity misc Ionization energy misc Bond dissociation energy misc Resorcinol and catechol derivatives misc Hydrogen bond
topic_browse	misc Antioxidant capacity misc Ionization energy misc Bond dissociation energy misc Resorcinol and catechol derivatives misc Hydrogen bond
format_facet	Elektronische Aufsätze Aufsätze Elektronische Ressource
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title	The substituent effect on the antioxidant capacity of catechols and resorcinols
ctrlnum	(DE-627)SPR002075334 (SPR)s00214-016-1932-7-e
title_full	The substituent effect on the antioxidant capacity of catechols and resorcinols
author_sort	Ortega-Moo, Cristina
journal	Theoretical chemistry accounts
journalStr	Theoretical chemistry accounts
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author_browse	Ortega-Moo, Cristina Garza, Jorge Vargas, Rubicelia
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author-letter	Ortega-Moo, Cristina
doi_str_mv	10.1007/s00214-016-1932-7
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title_sort	substituent effect on the antioxidant capacity of catechols and resorcinols
title_auth	The substituent effect on the antioxidant capacity of catechols and resorcinols
abstract	Abstract The antioxidant capacity of polyphenols is widely recognized; especially, the catechol moiety is considered a key piece in the structure of natural compounds with this characteristic. The resorcinol is also a dihydroxybenzene that is present in natural antioxidants; however, fewer experimental and theoretical studies have been addressed to this moiety. This work reports a comparative study of the substituent effect on properties related to the antioxidant capacity, as energy ionization (I), and O–H bond dissociation enthalpy (BDE), to analyze the electron transfer and hydrogen atom transfer (HAT) mechanisms, in derivatives of phenols, catechols and resorcinols. In the set of substituents tested %$({-}\hbox {CH}_3, {-}\hbox {CH}_2\hbox {CH}_3, {-}(\hbox {CH}_2)_2{-}\hbox {CH}_3, {-}\hbox {CH}{=}\hbox {CH}_2, {-}\hbox {CH}{=}\hbox {CHCOOH}, {-}\hbox {COOH}%$ and %${-}\hbox {CO}(\hbox {CH}_2)_4{-}\hbox {CH}_3)%$ electron-withdrawing and electron-donating groups, including alkyl chains, are considered. We found that electron-donating substituents reduce I and O–H BDE of resorcinols and catechols derivatives. In addition, the length of the alkyl chains is not relevant on resorcinols neither on catechols. With regard to the HAT process, a double bond in a substituent favors it, while the –COOH group shows a contrary effect. The combination of a double bond with a –COOH group, in the substituent, increases the BDE and reduces the electron donor capacity, and this result suggests that this combination induces a reduction in the antioxidant capacity in one polyphenol compound. In several reports, an intramolecular hydrogen bond has been proposed within to the most stable structure of catechol. However, by using arguments from the atoms in molecules approach and the electron localization function, we show that such an interaction is not relevant to stabilize this conformation and consequently and this is the reason that explains the unimportance of this interaction in the properties studied here and in previous studies. © Springer-Verlag Berlin Heidelberg 2016
abstractGer	Abstract The antioxidant capacity of polyphenols is widely recognized; especially, the catechol moiety is considered a key piece in the structure of natural compounds with this characteristic. The resorcinol is also a dihydroxybenzene that is present in natural antioxidants; however, fewer experimental and theoretical studies have been addressed to this moiety. This work reports a comparative study of the substituent effect on properties related to the antioxidant capacity, as energy ionization (I), and O–H bond dissociation enthalpy (BDE), to analyze the electron transfer and hydrogen atom transfer (HAT) mechanisms, in derivatives of phenols, catechols and resorcinols. In the set of substituents tested %$({-}\hbox {CH}_3, {-}\hbox {CH}_2\hbox {CH}_3, {-}(\hbox {CH}_2)_2{-}\hbox {CH}_3, {-}\hbox {CH}{=}\hbox {CH}_2, {-}\hbox {CH}{=}\hbox {CHCOOH}, {-}\hbox {COOH}%$ and %${-}\hbox {CO}(\hbox {CH}_2)_4{-}\hbox {CH}_3)%$ electron-withdrawing and electron-donating groups, including alkyl chains, are considered. We found that electron-donating substituents reduce I and O–H BDE of resorcinols and catechols derivatives. In addition, the length of the alkyl chains is not relevant on resorcinols neither on catechols. With regard to the HAT process, a double bond in a substituent favors it, while the –COOH group shows a contrary effect. The combination of a double bond with a –COOH group, in the substituent, increases the BDE and reduces the electron donor capacity, and this result suggests that this combination induces a reduction in the antioxidant capacity in one polyphenol compound. In several reports, an intramolecular hydrogen bond has been proposed within to the most stable structure of catechol. However, by using arguments from the atoms in molecules approach and the electron localization function, we show that such an interaction is not relevant to stabilize this conformation and consequently and this is the reason that explains the unimportance of this interaction in the properties studied here and in previous studies. © Springer-Verlag Berlin Heidelberg 2016
abstract_unstemmed	Abstract The antioxidant capacity of polyphenols is widely recognized; especially, the catechol moiety is considered a key piece in the structure of natural compounds with this characteristic. The resorcinol is also a dihydroxybenzene that is present in natural antioxidants; however, fewer experimental and theoretical studies have been addressed to this moiety. This work reports a comparative study of the substituent effect on properties related to the antioxidant capacity, as energy ionization (I), and O–H bond dissociation enthalpy (BDE), to analyze the electron transfer and hydrogen atom transfer (HAT) mechanisms, in derivatives of phenols, catechols and resorcinols. In the set of substituents tested %$({-}\hbox {CH}_3, {-}\hbox {CH}_2\hbox {CH}_3, {-}(\hbox {CH}_2)_2{-}\hbox {CH}_3, {-}\hbox {CH}{=}\hbox {CH}_2, {-}\hbox {CH}{=}\hbox {CHCOOH}, {-}\hbox {COOH}%$ and %${-}\hbox {CO}(\hbox {CH}_2)_4{-}\hbox {CH}_3)%$ electron-withdrawing and electron-donating groups, including alkyl chains, are considered. We found that electron-donating substituents reduce I and O–H BDE of resorcinols and catechols derivatives. In addition, the length of the alkyl chains is not relevant on resorcinols neither on catechols. With regard to the HAT process, a double bond in a substituent favors it, while the –COOH group shows a contrary effect. The combination of a double bond with a –COOH group, in the substituent, increases the BDE and reduces the electron donor capacity, and this result suggests that this combination induces a reduction in the antioxidant capacity in one polyphenol compound. In several reports, an intramolecular hydrogen bond has been proposed within to the most stable structure of catechol. However, by using arguments from the atoms in molecules approach and the electron localization function, we show that such an interaction is not relevant to stabilize this conformation and consequently and this is the reason that explains the unimportance of this interaction in the properties studied here and in previous studies. © Springer-Verlag Berlin Heidelberg 2016
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container_issue	7
title_short	The substituent effect on the antioxidant capacity of catechols and resorcinols
url	https://dx.doi.org/10.1007/s00214-016-1932-7
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author2	Garza, Jorge Vargas, Rubicelia
author2Str	Garza, Jorge Vargas, Rubicelia
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doi_str	10.1007/s00214-016-1932-7
up_date	2024-07-04T01:43:06.371Z
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The substituent effect on the antioxidant capacity of catechols and resorcinols

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