IR, Proton, and Carbon-13 NMR Spectral Characterization of Some Chiral and Achiral Aminophosphines and Their Selenides

Abstract

Though aminophosphines have been known for a century, and a large variety of such compounds has been synthesized for different aspects of their chemistry, until now, no examples are available on phosphines containing three different amino substituents. In this study, the first examples of such chiral tris(amino)phosphines and o-phenylenedioxo(amino)phosphines were successfully synthesized using condensation reactions, and they were converted to their respective selenides using a simple oxidative addition reaction. The compounds are characterized by IR, ¹H, and ¹³C NMR spectral techniques, and the spectral aspects are presented. The spectral studies (i) indicated that they are indeed powerful tools for structural elucidation of compounds; (ii) showed the effect of heavier selenium atom on the P–N bond rotation process; and (iii) further supported the fact that dipolar structure predominates over the π-bond structure for the aminophosphine selenides.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

Keywords:

• Aminophosphine selenides
• aminophosphines
• chiral aminophosphine selenides
• chiral aminophosphines
• dynamic NMR

Acknowledgments

J.G. thanks IITM, Chennai, India for financial support. SAIF, IITM, Chennai, India is gratefully acknowledged for NMR facilities.