A DFT Study on Intramolecular Hydrogen Bond in Substituted Catechols and Their Radicals  

作　　者：Hong Yu ZHANG You Min SUN 等 

机构地区：[1]LaboratoryforComputationalBiology,ShandongProvincialResearchCenterforBioinformaticEngineeringandTechnique,ShandongUniversityofTechnology,Zibo255049 [2]InstituteofTheoreticalChemistry,S

出　　处：《Chinese Chemical Letters》2003年第2期209-212,共4页中国化学快报（英文版）

基　　金：supported by the National Natural Science Foundation of China (Grant No. 30100035).

摘　　要：Density functional theory (DFT) at B3LYP/6-31G(d,p) level was employed to calculate intramolecular hydrogen bond enthalpies (HIHB), O-H charge differences, O-H bond lengths and bond orders for various substituted catechols and their radicals generated after H-abstraction. It was found that although the charge difference between hydrogen-bonded H and O played a role in determining HIHB, HIHB was mainly governed by the hydrogen bond length. As the oxygen-centered radical has great tendency to form a chemical bond with the H atom, hydrogen bond lengths in catecholic radicals are systematically shorter than those in catechols. Hence, the HIHB for the former are higher than those for the latter.Density functional theory (DFT) at B3LYP/6-31G(d,p) level was employed to calculate intramolecular hydrogen bond enthalpies (HIHB), O-H charge differences, O-H bond lengths and bond orders for various substituted catechols and their radicals generated after H-abstraction. It was found that although the charge difference between hydrogen-bonded H and O played a role in determining HIHB, HIHB was mainly governed by the hydrogen bond length. As the oxygen-centered radical has great tendency to form a chemical bond with the H atom, hydrogen bond lengths in catecholic radicals are systematically shorter than those in catechols. Hence, the HIHB for the former are higher than those for the latter.

关 键 词：CATECHOL catecholic radical density functional theory intramolecular hydrogen bond. 

分 类 号：R977.9[医药卫生—药品] O641.[医药卫生—药学]