2021
DOI: 10.1021/acs.jpca.0c11183
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Coexistence of Intra- and Intermolecular Hydrogen Bonds: Salicylic Acid and Salicylamide and Their Thiol Counterparts

Abstract: The ωB97-XD/6-311++G(d,p) calculations were carried out on dimers and monomers of salicylic acid and salicylamide as well as on their thiol counterparts; different conformations of these species were considered. The searches through the Cambridge Structural Database were performed to find related structures; thus the analysis of results of these searches is presented. Various approaches were applied to analyze inter- and intramolecular hydrogen bonds occurring in the above-mentioned species: natural bond orbit… Show more

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Cited by 13 publications
(18 citation statements)
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“…Recently, the core-valence bifurcation (CVB) index has been widely used to study the nature of IHBs. It is a method of investigating the strength of IHBs using the idea of topological analysis of an electron localization function (ELF). Commonly, if the CVB index is more negative, it means that the IHB is stronger. The CVB index of very strong IHBs can be highly negative, that of medium strong IHBs is generally near 0, and that of weaker IHBs normally is obviously positive.…”
Section: Resultsmentioning
confidence: 99%
“…Recently, the core-valence bifurcation (CVB) index has been widely used to study the nature of IHBs. It is a method of investigating the strength of IHBs using the idea of topological analysis of an electron localization function (ELF). Commonly, if the CVB index is more negative, it means that the IHB is stronger. The CVB index of very strong IHBs can be highly negative, that of medium strong IHBs is generally near 0, and that of weaker IHBs normally is obviously positive.…”
Section: Resultsmentioning
confidence: 99%
“…However, IMHB are the well-studied phenomenon, and a large number of articles are devoted to the quantitative assessment of the IMHB strength. [30][31][32][33][34][35][36][37][38][39][40][41][42][43][55][56][57][58][59][60][61][62][63][64][65] Moreover, there is a widely used energy scale of hydrogen bonds by which the IMHB strength are divided into weak, moderate and strong ones. 66,67 However, the PPE energy scale does not exist, since this phenomenon has been studied at a qualitative level without energy quantification.…”
Section: Energy Scale For Push-pull Effectmentioning
confidence: 99%
“…Among hydrogen bonds, the so‐called resonance‐assisted hydrogen bonds (RAHBs) play a special role, as they are extremely strong and cause an appreciable change in the structure of the molecules involved in such an interaction. The RAHB concept, introduced by Gilli and co‐workers in 1989, 9 has been repeatedly questioned and revised, 10–17 but still remains generally accepted 18–32 . A classical RAHB concept assumes that a enhance in the strength of H‐bond takes place due to the resonance assistance causing the synergistic effect through an increase of the electron delocalization across the π‐conjugated fragment connecting the H‐bond donor and acceptor atoms 33,34 .…”
Section: Introductionmentioning
confidence: 99%
“…The RAHB concept, introduced by Gilli and co-workers in 1989, 9 has been repeatedly questioned and revised, [10][11][12][13][14][15][16][17] but still remains generally accepted. [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32] A classical RAHB concept assumes that a enhance in the strength of H-bond takes place due to the resonance assistance causing the synergistic effect through an increase of the electron delocalization across the π-conjugated fragment connecting the H-bond donor and acceptor atoms. 33,34 As a consequence, the Hbond donor gains a positive charge whereas the H-bond acceptor increases negative charge that, in turn, magnifies an electrostatic contribution to the total H-bond energy.…”
Section: Introductionmentioning
confidence: 99%