Energetics and Reactivity of Morpholine and Thiomorpholine: A Joint Experimental and Computational Study
authors Freitas, VLS; Gomes, JRB; da Silva, MDMCR
nationality International
journal JOURNAL OF CHEMICAL AND ENGINEERING DATA
keywords HOMODESMOTIC REACTIONS; CYCLIC HYDROCARBONS; MICROWAVE-SPECTRUM; BOMB CALORIMETRY; THERMOCHEMISTRY; DERIVATIVES; ENTHALPIES; ENERGIES; HETEROCYCLES; COMBUSTION
abstract The influence of the heteroatoms in the conformational, energetic, and reactivity trends exhibited by morpholine and thiomorpholine isosteres was obtained from computational and experimental thermochemical studies. For those purposes, the gas-phase standard (p = 0.1 MPa) molar enthalpies of formation of the compounds, at T = 298.15 K, were determined from the experimental values of the standard molar. enthalpies of formation, in the liquid phase, and of the standard molar: enthalpies of vaporization, obtained by calorimetric techniques, and also from composite G3(MP2)// B3LYP calculations making use of appropriate working reactions. A very good agreement was found between the calculated and the experimental gas-phase enthalpies of formation. The computational study was further extended to the calculation of other gas-phase thermodynamic properties these compounds, namely, the N-H or C-H bond dissociation enthalpies, gas-phase acidities and basicitics, proton affinities and adiabatic ionization enthalpies, and the energies and structures of the conformational stereoisomers of morpholine and thiomorpholine.
publisher AMER CHEMICAL SOC
issn 0021-9568
year published 2014
volume 59
issue 2
beginning page 312
ending page 322
digital object identifier (doi) 10.1021/je4007162
web of science category Thermodynamics; Chemistry, Multidisciplinary; Engineering, Chemical
subject category Thermodynamics; Chemistry; Engineering
unique article identifier WOS:000331493300022
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journal impact factor 2.196
5 year journal impact factor 2.331
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