Thermochemical and structural study of a dibenzocycloheptane cyanoenamine

Stefan Perisanu; Iulia Contineanu; Ana Neacsu; Nigam P. Rath; James S. Chickos; Rafael Notario; Joel F. Liebman

doi:10.1007/s11224-013-0286-1

Thermochemical and structural study of a dibenzocycloheptane cyanoenamine

Stefan Perisanu, Iulia Contineanu, Ana Neacsu, Nigam P. Rath, James S. Chickos, Rafael Notario, Joel F. Liebman

University of Missouri-St. Louis

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

Abstract

The crystalline and gas phase enthalpy of formation of 5-cyano-7H-dibenzo-[a,c]-cyclohepten-6-amine (1) (142.0 ± 11.6 and 264 ± 20 kJ mol-1 , respectively) are reported. The sublimation enthalpy at T = 298.15 K for this compound was evaluated by combining the fusion enthalpy from DSC measurements adjusted to 298 K with estimated vaporization enthalpy. The experimental enthalpy of formation is discussed in relationship with values calculated at the G3(MP2)//B3LYP level of quantum chemical theory and by means of group additivity. The crystal structure of this compound was determined by X-ray crystallography and shown to exist entirely in the cyanoenamine form 1, i.e. not the tautomeric a-cyanoimine 2.

Original language	American English
Journal	Structural Chemistry
Volume	24
DOIs	https://doi.org/10.1007/s11224-013-0286-1
State	Published - Jan 12 2013

Keywords

Dibenzocycloheptane
Cyanoenamine
Enthalpies of combustion and of formation
DSC
G3(MP2)//B3LYP calculations
Crystal structure

Disciplines

Physical Chemistry

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@article{09353dfbcff94912abea233b6c4a4beb,

title = "Thermochemical and structural study of a dibenzocycloheptane cyanoenamine",

abstract = " The crystalline and gas phase enthalpy of formation of 5-cyano-7H-dibenzo-[a,c]-cyclohepten-6-amine (1) (142.0 ± 11.6 and 264 ± 20 kJ mol-1 , respectively) are reported. The sublimation enthalpy at T = 298.15 K for this compound was evaluated by combining the fusion enthalpy from DSC measurements adjusted to 298 K with estimated vaporization enthalpy. The experimental enthalpy of formation is discussed in relationship with values calculated at the G3(MP2)//B3LYP level of quantum chemical theory and by means of group additivity. The crystal structure of this compound was determined by X-ray crystallography and shown to exist entirely in the cyanoenamine form 1, i.e. not the tautomeric a-cyanoimine 2.",

keywords = "Dibenzocycloheptane, Cyanoenamine, Enthalpies of combustion and of formation, DSC, G3(MP2)//B3LYP calculations, Crystal structure",

author = "Stefan Perisanu and Iulia Contineanu and Ana Neacsu and Rath, {Nigam P.} and Chickos, {James S.} and Rafael Notario and Liebman, {Joel F.}",

note = "The crystalline and gas phase enthalpy of formation of 5-cyano-7 H-dibenzo-[a,c]-cyclohepten-6-amine ( 1) (142.0 ± 11.6 and 264 ± 20 kJ mol −1, respectively) are reported. The sublimation enthalpy at T = 298.15 K for this compound was evaluated by combining the fusion enthalpy from DSC measurements adjusted to 298 K with estimated vaporization enthalpy.",

year = "2013",

month = jan,

day = "12",

doi = "10.1007/s11224-013-0286-1",

language = "American English",

volume = "24",

journal = "Structural Chemistry",

}

TY - JOUR

T1 - Thermochemical and structural study of a dibenzocycloheptane cyanoenamine

AU - Perisanu, Stefan

AU - Contineanu, Iulia

AU - Neacsu, Ana

AU - Rath, Nigam P.

AU - Chickos, James S.

AU - Notario, Rafael

AU - Liebman, Joel F.

N1 - The crystalline and gas phase enthalpy of formation of 5-cyano-7 H-dibenzo-[a,c]-cyclohepten-6-amine ( 1) (142.0 ± 11.6 and 264 ± 20 kJ mol −1, respectively) are reported. The sublimation enthalpy at T = 298.15 K for this compound was evaluated by combining the fusion enthalpy from DSC measurements adjusted to 298 K with estimated vaporization enthalpy.

PY - 2013/1/12

Y1 - 2013/1/12

N2 - The crystalline and gas phase enthalpy of formation of 5-cyano-7H-dibenzo-[a,c]-cyclohepten-6-amine (1) (142.0 ± 11.6 and 264 ± 20 kJ mol-1 , respectively) are reported. The sublimation enthalpy at T = 298.15 K for this compound was evaluated by combining the fusion enthalpy from DSC measurements adjusted to 298 K with estimated vaporization enthalpy. The experimental enthalpy of formation is discussed in relationship with values calculated at the G3(MP2)//B3LYP level of quantum chemical theory and by means of group additivity. The crystal structure of this compound was determined by X-ray crystallography and shown to exist entirely in the cyanoenamine form 1, i.e. not the tautomeric a-cyanoimine 2.

AB - The crystalline and gas phase enthalpy of formation of 5-cyano-7H-dibenzo-[a,c]-cyclohepten-6-amine (1) (142.0 ± 11.6 and 264 ± 20 kJ mol-1 , respectively) are reported. The sublimation enthalpy at T = 298.15 K for this compound was evaluated by combining the fusion enthalpy from DSC measurements adjusted to 298 K with estimated vaporization enthalpy. The experimental enthalpy of formation is discussed in relationship with values calculated at the G3(MP2)//B3LYP level of quantum chemical theory and by means of group additivity. The crystal structure of this compound was determined by X-ray crystallography and shown to exist entirely in the cyanoenamine form 1, i.e. not the tautomeric a-cyanoimine 2.

KW - Dibenzocycloheptane

KW - Cyanoenamine

KW - Enthalpies of combustion and of formation

KW - DSC

KW - G3(MP2)//B3LYP calculations

KW - Crystal structure

UR - https://link.springer.com/content/pdf/10.1007%2Fs11224-013-0286-1.pdf

UR - https://rd.springer.com/content/pdf/10.1007%2Fs11224-013-0286-1.pdf

U2 - 10.1007/s11224-013-0286-1

DO - 10.1007/s11224-013-0286-1

M3 - Article

VL - 24

JO - Structural Chemistry

JF - Structural Chemistry

ER -

Thermochemical and structural study of a dibenzocycloheptane cyanoenamine

Abstract

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