Abstract
AbstractThe 14N nuclear quadrupole resonance (NQR) spectra of several nitrogen mustard compounds are reported and analyzed in the framework of the Townes and Dailey theory. For the aniline derivatives, a correlation exists between l–σ (where l is the nitrogen lone pair electron density and σ the average NC sigma‐bond electron density) and the enhanced Hammett sigma constant σ−. An improved correlation is obtained between l–σ and σR−, which emphasizes the importance of resonance effects in determining l–σ. The increase of hydrolysis and alkylation rates with increasing values of l–σ is in agreement with the identification of the aziridinium ion as the intermediate in aromatic nitrogen mustard hydrolysis and alkylation. A possible correlation is noted between the 35Cl NQR spectra for some of the mustards and measures of toxic and antitumor activity.
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