Aromaticity in cyanuric acid.
This study analyzes the aromatic nature of cyanuric acid (hexahydrotriazine) and some of its derivatives, in terms of aromatic stabilization energy (ASE) and electronic behavior. The simplest molecule (C(3)N(3)O(3)H(3)) is the most aromatic item out of the entire set, but some of the others also display aromatic character. The structure of all the rings is analyzed considering their molecular orbitals as well as studying the inductive effect.
Pérez-Manríquez
Liliana
L
Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Coyoacán, México City, Mexico.
Cabrera
Armando
A
Sansores
Luis Enrique
LE
Salcedo
Roberto
R
D001592:Benzyl Alcohols / Q000737:chemistry; D004563:Electrochemistry; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D010696:Phloroglucinol / Q000737:chemistry; D014227:Triazines / Q000737:chemistry*
D001592:Benzyl Alcohols; D006841:Hydrocarbons, Aromatic; D007659:Ketones; D014227:Triazines; D010696:Phloroglucinol; C004632:cyanuric acid
Org Lett. 2001 Jun 14;3(12):1921-4
11405745
Chem Rev. 2001 May;101(5):1541-66
11710232
J Phys Chem B. 2007 Jun 21;111(24):6634-42
17455975
Inorg Chem. 2003 Jul 28;42(15):4513-5
12870937
J Am Chem Soc. 2007 Dec 26;129(51):16057-71
18052376
Chem Rev. 2001 May;101(5):1385-419
11710226
Phys Rev B Condens Matter. 1992 Jun 15;45(23):13244-13249
10001404
J Am Chem Soc. 2001 Aug 8;123(31):7518-33
11480972
Chemistry. 2006 Mar 20;12(10):2663-79
16491494
Phys Rev A Gen Phys. 1988 Sep 15;38(6):3098-3100
9900728