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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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Contributing structures in cyanuric acid
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Sch1: Contributing structures in cyanuric acid

Mentions: The HOMA results are shown in Table 2. Several factors emerging from these results should be noted. First, the most aromatic species in this set is the enol form of cyanuric acid (5b), with the next strongest value corresponding to the keto form of the same derivative. Likewise, this result suggests that the enol form will turn out to be the most stable isomer. However, the energy results indicate the contrary, and as outlined above the explanation for this phenomenon arises from the existence of a zwitterionic species which converts from 5 to become 5b, based on the proton mobility of both species [29]. On the other hand, the same zwitterionic species is also described as having a canonical structure as in 5, presented in Scheme 1.Table 2


Aromaticity in cyanuric acid.

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

Contributing structures in cyanuric acid
© Copyright Policy
Related In: Results  -  Collection

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

Sch1: Contributing structures in cyanuric acid
Mentions: The HOMA results are shown in Table 2. Several factors emerging from these results should be noted. First, the most aromatic species in this set is the enol form of cyanuric acid (5b), with the next strongest value corresponding to the keto form of the same derivative. Likewise, this result suggests that the enol form will turn out to be the most stable isomer. However, the energy results indicate the contrary, and as outlined above the explanation for this phenomenon arises from the existence of a zwitterionic species which converts from 5 to become 5b, based on the proton mobility of both species [29]. On the other hand, the same zwitterionic species is also described as having a canonical structure as in 5, presented in Scheme 1.Table 2

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