Busca avançada
Ano de início
Entree
(Referência obtida automaticamente do Web of Science, por meio da informação sobre o financiamento pela FAPESP e o número do processo correspondente, incluída na publicação pelos autores.)

Halogen center dot center dot center dot halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene

Texto completo
Autor(es):
Foi, Ana [1] ; Correa, Rodrigo S. [2] ; Ellena, Javier [3] ; Doctorovich, Fabio [1] ; Di Salvo, Florencia [1]
Número total de Autores: 5
Afiliação do(s) autor(es):
[1] Univ Buenos Aires, INQUIMAE CONICET, Fac Ciencias Exactas Nat, Dept Quim Inorgan Anal & Quim Fis, Buenos Aires, DF - Argentina
[2] Univ Fed Sao Carlos, Dept Quim, UFSCar, BR-13561901 Sao Carlos, SP - Brazil
[3] Univ Sao Paulo, Inst Fis Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil
Número total de Afiliações: 3
Tipo de documento: Artigo Científico
Fonte: Journal of Molecular Structure; v. 1059, p. 1-7, FEB 5 2014.
Citações Web of Science: 6
Resumo

A new polymorph of 9,10-dichloroanthracene (9,10-DCA) namely as gamma form, was obtained. The crystal structure of the gamma polymorphic system showed an orthorhombic P2(1)2(1)2(1) space group with a = 3.8957(2) angstrom, b = 15.9383(5) angstrom, c = 17.3107(7) angstrom, alpha = beta = gamma = 90 degrees, while the other polymorphs, alpha and beta, crystallized in P2(1)/a and P-1 ones, respectively. The intermolecular geometries of gamma form were analyzed showing that the crystalline self-assembly of this new polymorph of the 9,10-DCA is stabilized by non-classical C-H center dot center dot center dot Cl hydrogen bonds, pi-pi stacking interactions, and mainly by a Cl center dot center dot center dot Cl interactions. Structural parameters confirmed the halogen center dot center dot center dot halogen contacts correspond to the Type II geometry. Complementary, electronic structure calculations were performed in other to estimate the energetic contribution of the observed intermolecular interactions in the crystal packing of the new system. Density Functional Theory (DFT) considering empirical dispersion corrections (named as DFT-D) and MP2 correlated very well and showed energy values according to previously reported related compounds (e.g., the energy for the Cl center dot center dot center dot Cl is -5.37 and -3.25 kcal mol(-1) for MP2/6-31+G{*}{*} and B2PLYP-D/6-31+G{*}{*}, respectively). On the other hand, and as expected, DFT using B3LYP as functional was not able to describe properly the studied intermolecular interactions. Moreover, it even predicts repulsive energies for most of the analyzed arrangements. (C) 2013 Elsevier B.V. All rights reserved. (AU)

Processo FAPESP: 09/08131-1 - Complexos de rutênio com ligantes de interesse biológico: aspectos químicos, estruturais e avaliação de suas citotoxicidades em células tumorais
Beneficiário:Rodrigo de Souza Corrêa
Linha de fomento: Bolsas no Brasil - Doutorado