Premium
The interaction of methylglyoxal with methylamine and the triplet state
Author(s) -
Abdulnur Suheil F.
Publication year - 2009
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560120723
Subject(s) - methylglyoxal , chemistry , glyoxal , methylamine , crotonaldehyde , conjugated system , polymerization , molecule , photochemistry , schiff base , triplet state , polymer chemistry , computational chemistry , organic chemistry , polymer , enzyme , catalysis
The interaction of methylglyoxal (MG) with methylamine (MA) to form a Schiff base (SB) is investigated theoretically using the INDO technique. The following findings are reported: (a) MG, SB, and the Schiff base of glyoxal (G) have much lower triplet state energies than G or dimethyl‐glyoxal; (b) these molecules and the conjugated polymerizing ones butadiene, isoprene, acrolein, and crotonaldehyde have a similar π LEMO over the conjugating atoms; and (c) the formation of a hemiacetal intermediate prior to SB formation is very favored energetically, but hydration of MG can seriously compete against it. A possible polymerization of the Schiff bases formed by the interaction of MG with the –NH 2 groups of protein molecules could stabilize the structured β state and contribute to the “brakelike” action of dicarbonyls on cell proliferation in Szent‐Györgyi's theory of cancer.