Using the Pyridine and Quinuclidine Scaffolds for Superbases: A DFT Study

被引：34

作者：

Bachrach, Steven M. ^{[1
]}

Wilbanks, Cecily C. ^{[1
]}

机构：

[1] Trinity Univ, Dept Chem, San Antonio, TX 78212 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 08期

关键词：

ORGANIC SUPERBASES; PROTON AFFINITY; HYDROGEN-BONDS; MOLECULES; POLYAMINOPHOSPHAZENES; MICROSOLVATION; DERIVATIVES; SPONGES; DESIGN; BASES;

D O I：

10.1021/jo100295s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,6-Disubstituted pyridines and 2,6,7-trisubstituted quinuclidines are screened as potential strong bases. The relative proton affinities of the bases are computed at PBE1PBE/6-311 G(d,p) in the gas phase and in the solution phase (THF) at the same level with the IEFPCM treatment. Basicities are enhanced by the lone-pair possessing atoms on the substituents' arms stabilizing the conjugate acid through hydrogen bonding. The strongest bases are 2,6-bis(3-methoxy-2-furyl)-4-dimethylaminopyridine and 2,6-di(2-dimethylaminoethyl)pyridine

引用

页码：2651 / 2660

页数：10

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