Electronic origin of pyridinyl N as a better hydrogen-bonding acceptor than carbonyl O

Tonglei Li, Alessandra Mattei, and Panpan Zhou
CrystEngComm, 13:6356-6360, 2011

Abstract (from publisher): A diarylamine compound, 2-(phenylamino)nicotinic acid, can form either the carboxyl acid–acid dimer or acid–pyridine chain in its polymorphic structures. Quantum mechanical calculations indicate that the hydrogen-bonding strength of the heterosynthon is stronger. Conceptual density functional theory is then used to understand the fundamental cause of pyridine N being a better hydrogen-bonding acceptor.

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