Issue 28, 2015

Solid-state identity of 2-hydroxynicotinic acid and its polymorphism

Abstract

2-Hydroxynicotinic acid (2-HNA), a derivative of nicotinic acid, was found to exist in four polymorphs. In the solid state, 2-HNA is actually present as its tautomer, 2-oxo-1,2-dihydro-3-pyridinecarboxylic acid (2-ODHPCA). The polymorphism stems from distinctive packing arrangements of the molecules, and the formation of the distinct polymorphs can be affected by using various acidic additives. The thermal behaviors of the four polymorphs indicate that form I is the most stable at elevated temperature, form II converts into form I during heating, and forms III and IV transform into form II when heated. Theoretical studies showed that 2-ODHPCA is more energetically favored than 2-HNA. Condensed Fukui functions and the dual descriptor were used jointly to examine the local preference of hydrogen bonding in the crystal. Lattice energy calculations were conducted to further evaluate energetic properties of the system.

Graphical abstract: Solid-state identity of 2-hydroxynicotinic acid and its polymorphism

  • This article is part of the themed collection: Polymorphism

Supplementary files

Article information

Article type
Paper
Submitted
19 Nov 2014
Accepted
05 Jan 2015
First published
07 Jan 2015

CrystEngComm, 2015,17, 5195-5205

Solid-state identity of 2-hydroxynicotinic acid and its polymorphism

S. Long, P. Zhou, K. L. Theiss, M. A. Siegler and T. Li, CrystEngComm, 2015, 17, 5195 DOI: 10.1039/C4CE02290D

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