Application of roof-shape amines as chiral solvating agents for discrimination of optically active acids by NMR spectroscopy: study of match-mismatch effect and crystal structure of the diastereomeric salts

TitleApplication of roof-shape amines as chiral solvating agents for discrimination of optically active acids by NMR spectroscopy: study of match-mismatch effect and crystal structure of the diastereomeric salts
Publication TypeJournal Article
Year of Publication2016
AuthorsGupta, R, Gonnade, RG, Bedekar, AV
JournalJournal of Organic Chemistry
Volume81
Issue17
Pagination7384-7392
Date PublishedSEP
ISSN0022-3263
Abstract

Optically active roof-shape amines were prepared and scanned as chiral solvating agents to study molecular recognition of acids by NMR analysis. Three types of amines were studied to establish a match mismatch effect for structurally diverse acid analytes. Single-crystal X-ray diffraction analysis was performed on the diastereomeric salts of roof shape amines and both isomers of mandelic acid to establish molecular conformation and correlate the absolute configuration with the observed NMR shift. The present system also recognizes the two isomers of weakly acidic BINOL and its derivatives.

DOI10.1021/acs.joc.6b00935
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.785

Divison category: 
Center for Material Characterization (CMC)