ISSN:
1572-9001
Keywords:
Proton sponges
;
proton transfer
;
basicity
;
monosubstituted benzenes
;
LBHB
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1026561820090
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