TY - JOUR
T1 - Thermochemical study of 1-acetyl vinyl p-nitrobenzoate
T2 - Vinyl bond enthalpy in captodative olefins
AU - Rojas, Aarón
AU - Valdés-Ordoñez, Alejandro
AU - Martínez-Herrera, Melchor
AU - Torres, Luis Alfonso
AU - Campos, Myriam
AU - Hernández-Obregón, Javier
AU - Herrera, Rafael
AU - Tamariz, Joaquín
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/5/21
Y1 - 2015/5/21
N2 - Captodative olefins are highly reactive and selective substrates in Diels-Alder and 1,3-dipolar cycloadditions. Seeking an explanation of this fact based on molecular energetics, the thermochemical analysis of 1-acetyl vinyl p-nitrobenzoate, a captodative olefin, has been performed using semi-micro-combustion calorimetry, effusion measurements through a quartz crystal microbalance, and differential scanning calorimetry. The molar standard combustion energy and enthalpy as well as the molar standard formation enthalpy are reported along with sublimation and melting enthalpies. From these data, experimental formation enthalpy of the gas-phase is derived and compared with the theoretical value calculated through the density functional theory procedure. The olefinic bond enthalpy is also computed from experimental data, and the relevance of the results is discussed.
AB - Captodative olefins are highly reactive and selective substrates in Diels-Alder and 1,3-dipolar cycloadditions. Seeking an explanation of this fact based on molecular energetics, the thermochemical analysis of 1-acetyl vinyl p-nitrobenzoate, a captodative olefin, has been performed using semi-micro-combustion calorimetry, effusion measurements through a quartz crystal microbalance, and differential scanning calorimetry. The molar standard combustion energy and enthalpy as well as the molar standard formation enthalpy are reported along with sublimation and melting enthalpies. From these data, experimental formation enthalpy of the gas-phase is derived and compared with the theoretical value calculated through the density functional theory procedure. The olefinic bond enthalpy is also computed from experimental data, and the relevance of the results is discussed.
UR - http://www.scopus.com/inward/record.url?scp=84930226964&partnerID=8YFLogxK
U2 - 10.1021/acs.jpca.5b01526
DO - 10.1021/acs.jpca.5b01526
M3 - Artículo
SN - 1089-5639
VL - 119
SP - 4953
EP - 4960
JO - Journal of Physical Chemistry A
JF - Journal of Physical Chemistry A
IS - 20
ER -