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

共 50 条

[31] Adsorption and spin polarization of pyridine on Fe/W(110) interface: A DFT study
Nharangatt, Bijoy
Chatanathodi, Raghu
COMPUTATIONAL MATERIALS SCIENCE, 2021, 199
[32] Pyridine and s-triazine as building blocks of nonionic organic superbases -: a density functional theory B3LYP study
Despotovic, Ines
Kovacevic, Borislav
Maksic, Zvonimir B.
NEW JOURNAL OF CHEMISTRY, 2007, 31 (03) : 447 - 457
[33] DFT study of hydrogen bond bridging mode of pyridine and diazenes in water environment
Singh, Deepa
Srivastava, Sunil K.
Ojha, Animesh K.
Asthana, B. P.
Singh, Ranjan K.
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2007, 819 (1-3): : 88 - 94
[34] Direct esterification of p-nitrobenzoic acid with n-butanol using diethyl chlorophosphate in pyridine: A DFT study
Zhang, Wenjing
Zhu, Yanyan
Wei, Donghui
Zhang, Cong
Sun, Dongzhen
Tang, Mingsheng
COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2011, 963 (01) : 13 - 17
[35] SYNTHESIS AND STRUCTURAL STUDY OF QUINUCLIDINE SPIRO DERIVATIVES
TRIGO, GG
MARTINEZ, M
GALVEZ, E
CABEZAS, R
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (08) : 1507 - 1511
[36] Leveraging the properties of pyridine derivatives using DFT analysis to achieve breakthroughs in supercapacitance advancements
Ranchani, A. Amala Jeya
Reeda, V. S. Jeba
Divya, P.
Suja, R.
Jothy, V. Bena
IONICS, 2024, 30 (10) : 6451 - 6473
[37] Exploring photochemistry of 2-(phenylazo)pyridine dye by using TDDFT/DFT methods
Tongying, Pornthip
Yoopensuk, Suthirat
Leesakul, Nararak
Tantirungrotechai, Yuthana
CANADIAN JOURNAL OF CHEMICAL ENGINEERING, 2012, 90 (04): : 860 - 864
[38] DFT study of low-energy electron interaction with pyridine, pyrazine and their halo derivatives
Tanska, Natalia
EUROPEAN PHYSICAL JOURNAL D, 2021, 75 (04):
[39] Combined MCD/DFT/TDDFT Study of the Electronic Structure of Axially Pyridine Coordinated Metallocorroles
Rhoda, Hannah M.
Crandall, Laura A.
Geier, G. Richard, III
Ziegler, Christopher J.
Nemykin, Victor N.
INORGANIC CHEMISTRY, 2015, 54 (10) : 4652 - 4662
[40] DFT study of low-energy electron interaction with pyridine, pyrazine and their halo derivatives
Natalia Tańska
The European Physical Journal D, 2021, 75

← 1 2 3 4 5 →