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13 C and 1 H NMR studies of some aminoarsonium chlorides
Author(s) -
Watkins C. L.,
Krannich L. K.,
Kanjolia R. K.,
Srivastava D. K.
Publication year - 1989
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260270703
Subject(s) - chemistry , arsine , substituent , delocalized electron , nmr spectra database , carbon 13 nmr , salt (chemistry) , proton nmr , medicinal chemistry , spectral line , stereochemistry , organic chemistry , catalysis , physics , astronomy , phosphine
Abstract 13 C and 1 H NMR spectral data for a homologous series of tertiary arsines (R 3 As, where R = Me, Et, n ‐Pr and Ph), aminoarsines and arsonium and aminoarsonium salts are reported and discussed. In nearly all cases, quaternization of the tertiary arsine to its corresponding arsonium or aminoarsonium salt causes a decrease in the magnitude of δ c . These results are compared with those from an analogous study on the quaternization of tertiary phosphines, R 3 P. A discussion of the factors that affect the relative magnitudes of δ c and R 3 As and R 3 P is given. Hammett‐Taft dual substituent parameter analysis was used to show that the positive charge on the arsenic in the atomatic quaternary salts is delocalized by an inductive mechanism. The 1 H NMR spectra of the n‐propyl‐ and phenyl‐containing compounds are non‐first order. The δ H and n J (HH) values were determined by iterative computer analysis. Likewise, the n J (CH) values for the phenyl carbons of [Ph 3 AsNH 2 ]Cl and [Ph 3 AsNHMe]Cl were determined from the coupled 13 C NMR spectra.