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Aromaticity in cyanuric acid.

Pérez-Manríquez L, Cabrera A, Sansores LE, Salcedo R - J Mol Model (2010)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Coyoacán, México City, Mexico.

ABSTRACT
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.

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Phloroglucinol (a) enol form (b) keto form
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Fig3: Phloroglucinol (a) enol form (b) keto form

Mentions: These results can be compared to those for a different molecule that has little resemblance to cyanuric acid, in order to evaluate the suitability of the HOMA method for the present study. This molecule is 1,2,5-Trihydroxybenzene, commonly known as Phloroglucinol (see Fig. 3). With respect to this species, it has the same three OH substituents, but in this case it is expected to be very difficult to detect the phenomenon of tautomerism because the hydrogen atoms which leave the hydroxyl groups converting to the keto form should unite with the free carbon atoms on the ring, resulting in a severe distortion. The HOMA results for the enol and keto forms of this species are 0.9995 and 0.357 respectively. The difference between these two cases is larger than those in the case of cyanuric acid because this last is constituted from nitrogen atoms with dangling bonds which favor the keto-enolic equilibrium. Thus our comparison is useful in this context to validate the use of the HOMA method.Fig. 3


Aromaticity in cyanuric acid.

Pérez-Manríquez L, Cabrera A, Sansores LE, Salcedo R - J Mol Model (2010)

Phloroglucinol (a) enol form (b) keto form
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3102184&req=5

Fig3: Phloroglucinol (a) enol form (b) keto form
Mentions: These results can be compared to those for a different molecule that has little resemblance to cyanuric acid, in order to evaluate the suitability of the HOMA method for the present study. This molecule is 1,2,5-Trihydroxybenzene, commonly known as Phloroglucinol (see Fig. 3). With respect to this species, it has the same three OH substituents, but in this case it is expected to be very difficult to detect the phenomenon of tautomerism because the hydrogen atoms which leave the hydroxyl groups converting to the keto form should unite with the free carbon atoms on the ring, resulting in a severe distortion. The HOMA results for the enol and keto forms of this species are 0.9995 and 0.357 respectively. The difference between these two cases is larger than those in the case of cyanuric acid because this last is constituted from nitrogen atoms with dangling bonds which favor the keto-enolic equilibrium. Thus our comparison is useful in this context to validate the use of the HOMA method.Fig. 3

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Coyoacán, México City, Mexico.

ABSTRACT
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.

Show MeSH