Colour Polymorphism of a Bis(quinoxaline) Compound

• Published in: European journal of organic chemistry Vol. 1999; no. 9; pp. 2119 - 2125
• Main Authors: Csikós, Éva, Ferenczy, György G., Ángyán, János G., Böcskei, Zsolt, Simon, Kálmán, Gönczi, Csaba, Hermecz, István
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag GmbH 01.09.1999; WILEY‐VCH Verlag GmbH; Wiley
• Subjects: Chemistry; Chemistry, Organic; Molecular mechanical calculations; Physical Sciences; Polymorphism; Quantum chemical calculations; Quinoxalines; Science & Technology; X-ray analysis; x-ray analysis; molecular mechanical calculations; NMDA RECEPTOR; GLYCINE-SITE; quantum chemical calculations; polymorphism; quinoxalines; SOLID-STATE
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/(SICI)1099-0690(199909)1999:9<2119::AID-EJOC2119>3.0.CO;2-J

Synthesis of 2(1H)‐quinoxalinone O‐(2′‐quinoxalinyl)oxime (3) results in two easily distinguishable crystal forms with different colours, providing a rare example of colour polymorphism. The crystal structures of the two forms have been determined and compared. Intermolecular interactions and light‐absorption characteristics of the polymorphs have been analysed by a mixed quantum chemical/molecular mechanical method. In one of the polymorphic forms the crystal field stabilises relatively high energy conformations by enhanced electrostatic interactions. The difference in the light absorption is found to be caused partly by a conformational difference of the molecules. The crystal field increases the difference in the absorption wavelengths and shift them towards higher values.