Solvent and substituent effects on the conformational equilibria and intramolecular hydrogen bonding of 4-substituted-2-hydroxybenzaidehydes

被引：7
|
作者：
Blanco, Sonia E. [1 ]
Ferretti, Ferdinando H. [1 ]
机构：
[1] Univ Nacl San Luis, Fac Quim Bioquim & Farm, Area Quim Fis, RA-5700 San Luis, Argentina
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 14期
关键词：
2-hydroxybenzaidehydes; conformational equilibria; intramolecular hydrogen bond; solvent and substituent effects; acity parameter; SCIPCM model; DFT method;
D O I：
10.1016/j.tetlet.2007.02.012
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
By applying the B3LYP/6-31G(d) method with the SCIPCM model on seven 4X substituted 2-hydroxybenzaldehydes, some structural characteristics related with their conformational equilibria and intramolecular hydrogen bonds have been clarified. The compounds are almost completely under the planar conformation characterized by a strong intramolecular hydrogen bond, which decreases in those solvents that possess a higher hydrogen bond donating capability and polarity. The substituents exert a marked influence on the conformational equilibrium constants and the strength of the IHB. Moreover, the excellent Hammett-type equations obtained support the proposed conformational reactions to quantify the IHB in the o-hydroxybenzaldehydes studied. (c) 2007 Elsevier Ltd. All rights reserved.
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页码：2577 / 2581
页数：5
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