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.

引用

页码：2577 / 2581

页数：5

共 22 条

[1] DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR [J].

BECKE, AD .

PHYSICAL REVIEW A, 1988, 38 (06) :3098-3100

[2]

CASTRO GT, 2004, INTERNET ELECT J MOL, V3, P684

[3]

Chen C, 1999, INT J QUANTUM CHEM, V74, P395, DOI 10.1002/(SICI)1097-461X(1999)74:4<395::AID-QUA3>3.0.CO

[4]

2-Q

[5]

CHEN C, 1998, HUAXUE, V56, P237

[6] Solvent effects .5. Influence of cavity shape, truncation of electrostatics, and electron correlation ab initio reaction field calculations [J].

Foresman, JB ;

Keith, TA ;

Wiberg, KB ;

Snoonian, J ;

Frisch, MJ .

JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (40) :16098-16104

[7]

Frisch M.J., 2004, Gaussian 03

[8]

Revision C.02

[9] An exception to the normal Mitsunobu reaction with phenols; the formation of hydrazones from salicylaldehydes [J].

Girard, M ;

Murphy, P ;

Tsou, NN .

TETRAHEDRON LETTERS, 2005, 46 (14) :2449-2452

[10] Organocatalytic synthesis of chiral benzopyrans [J].

Govender, Thavendran ;

Hojabri, Leila ;

Moghaddam, Frouz Matloubi ;

Arvidsson, Per I. .

TETRAHEDRON-ASYMMETRY, 2006, 17 (12) :1763-1767

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