Do nitrogen-containing oxocarbons exist? Predictions of their stability and aromaticity

Iñaki Morao; Mark A. Vincent; Ian H. Hillier

doi:10.1021/jp012889r

Do nitrogen-containing oxocarbons exist? Predictions of their stability and aromaticity

Iñaki Morao, Mark A. Vincent, Ian H. Hillier

Research output: Contribution to journal › Article › peer-review

Abstract

Density functional theory has been used to investigate the structure, stability and aromaticity of a series of nitrogen-containing oxocarbons, which are related to CnOn2- (n = 3-6). We have identified a large number of minimum-energy species which might be synthesized and calculated their aromaticity using the nucleus-independent chemical shift method of Schleyer. Successive substitution of carbon by nitrogen reduces their stability, as reflected in the calculated bond orders and dissociation energies. In general, there is no close correlation between the stability and π-aromaticity of the species studied.

Original language	English
Pages (from-to)	10689-10693
Number of pages	4
Journal	Journal of Physical Chemistry A
Volume	105
Issue number	47
DOIs	https://doi.org/10.1021/jp012889r
Publication status	Published - 29 Nov 2001

Keywords

Density functional theory (B3LYP; predictions of stability and aromaticity of N-contg. oxocarbons isoelectronic with the deltate, squarate, croconate, and rhodizonate series); Antiaromaticity; Aromaticity; Bond order; Decarbonylation enthalpy; Dissociation enthalpy; Isoelectronic sequence; Isomerization enthalpy; Substituent effects; Vibrational frequency (predictions of stability and aromaticity of N-contg. oxocarbons isoelectronic with the deltate, squarate, croconate, and rhodizonate series)

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title = "Do nitrogen-containing oxocarbons exist? Predictions of their stability and aromaticity",

abstract = "Density functional theory has been used to investigate the structure, stability and aromaticity of a series of nitrogen-containing oxocarbons, which are related to CnOn2- (n = 3-6). We have identified a large number of minimum-energy species which might be synthesized and calculated their aromaticity using the nucleus-independent chemical shift method of Schleyer. Successive substitution of carbon by nitrogen reduces their stability, as reflected in the calculated bond orders and dissociation energies. In general, there is no close correlation between the stability and π-aromaticity of the species studied.",

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author = "I{\~n}aki Morao and Vincent, {Mark A.} and Hillier, {Ian H.}",

year = "2001",

month = nov,

day = "29",

doi = "10.1021/jp012889r",

language = "English",

volume = "105",

pages = "10689--10693",

journal = "Journal of Physical Chemistry A",

issn = "1520-5215",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Do nitrogen-containing oxocarbons exist? Predictions of their stability and aromaticity

AU - Morao, Iñaki

AU - Vincent, Mark A.

AU - Hillier, Ian H.

PY - 2001/11/29

Y1 - 2001/11/29

N2 - Density functional theory has been used to investigate the structure, stability and aromaticity of a series of nitrogen-containing oxocarbons, which are related to CnOn2- (n = 3-6). We have identified a large number of minimum-energy species which might be synthesized and calculated their aromaticity using the nucleus-independent chemical shift method of Schleyer. Successive substitution of carbon by nitrogen reduces their stability, as reflected in the calculated bond orders and dissociation energies. In general, there is no close correlation between the stability and π-aromaticity of the species studied.

AB - Density functional theory has been used to investigate the structure, stability and aromaticity of a series of nitrogen-containing oxocarbons, which are related to CnOn2- (n = 3-6). We have identified a large number of minimum-energy species which might be synthesized and calculated their aromaticity using the nucleus-independent chemical shift method of Schleyer. Successive substitution of carbon by nitrogen reduces their stability, as reflected in the calculated bond orders and dissociation energies. In general, there is no close correlation between the stability and π-aromaticity of the species studied.

KW - Density functional theory (B3LYP; predictions of stability and aromaticity of N-contg. oxocarbons isoelectronic with the deltate, squarate, croconate, and rhodizonate series); Antiaromaticity; Aromaticity; Bond order; Decarbonylation enthalpy; Dissociatio

U2 - 10.1021/jp012889r

DO - 10.1021/jp012889r

M3 - Article

SN - 1520-5215

VL - 105

SP - 10689

EP - 10693

JO - Journal of Physical Chemistry A

JF - Journal of Physical Chemistry A

IS - 47

ER -

Do nitrogen-containing oxocarbons exist? Predictions of their stability and aromaticity

Abstract

Keywords

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