Basicity and proton transfer in proton sponges and related compounds:: An ab initio study

被引：22

作者：

Alkorta, I ^{[1
]}

Elguero, J ^{[1
]}

机构：

[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain

来源：

STRUCTURAL CHEMISTRY | 2000年 / 11卷 / 06期

关键词：

proton sponges; proton transfer; basicity; monosubstituted benzenes; LBHB;

D O I：

10.1023/A:1026561820090

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Theoretical calculations at the B3LYP/6-31G* level were carried out on a family of 1,8-diR-naphthalenes, which include the proton sponge (1,8-bisdimethylaminonaphthalene, R = NMe2) and other substituents (R = NH2, R = OH, R = CH3, R = F). Their basicity was compared with that of the corresponding monosubstituted benzenes. The dianion of 1,8-dihydroxynaphthalene should be a compound of extraordinary high basicity. The barriers to proton transfer, geometry, and density at the bond critical point of the hydrogen bond have been calculated and compared with experimental data when available.

引用

页码：335 / 340

页数：6

共 34 条

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ALDER RW, 1968, CHEM COMMUN, P723

[2] Carbon acidity and ring strain: A hybrid HF-DFT approach (Becke3LYP/6-311++G**) [J].