ISSN:
0947-3440
Keywords:
1-(1-Chloroalkyl)pyridinium halides
;
Amino-1H-1,2,4-triazole
;
Bis(onium) salts
;
Alkylations
;
Ab initio calculations
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
1-[(5-Amino-1-methyl-1H-1,2,4-triazol-4-ylium)(alkyl/aryl)-methyl]pyridinium dichlorides 3a-h [geminal bis(heteroarylium) salts] were synthesized in high yield from 5-amino-1-methyl-1H-1,2,4-triazole (6a) and the 1-[(alkyl/aryl)chloromethyl]pyridinium chlorides 1a-h under mild, neutral conditions. Analogous reactions of 1a and 1d with the isomeric 3-amino-1-methyl-1H-1,2,4-triazole (6b), carried out to support the spectroscopic analysis of the alkylation products 3a-h, likewise show exclusive alkylation at the N-4 atom of the 1H-1,2,4-triazole ring with formation of the isomeric 1-[(3-amino-1-methyl-1H-1,2,4-triazol-4-ylium)arylmethyl]pyridinium dichlorides 4a and 4d, respectively. Semiempirical MO and ab initio methods have been applied to predict the relative energies of isomers of 6, the activation barriers of the reaction of electrophiles with 6, and the relative energies of some product salts.
Additional Material:
7 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970417
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