145240 20241015122513.0 doi 10.1021/acs.cgd.7b00690 sideral 104042 ART-2017-104042 eng González, Lucía (orcid)0000-0002-7486-8502 Two-dimensional arrangements of bis(haloethynyl)benzenes combining halogen and hydrogen interactions 2017 The electronic distribution of some haloethynylbenzene derivatives may favor the formation of two-dimensional organizations by combining halogen and hydrogen bonds. In order to highlight this strategy, we have prepared seven cocrystals and analyzed their structures. 1,4-Bis(iodoethynyl)benzene, 1,4-bis(bromoethynyl)benzene, and 1,3-bis(iodoethynyl)benzene were used as halogen bond donors and 1,2-bis(4-pyridyl)ethylene, pyridazine, propanone, hexamethylenetetramine, and 2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (Tro¨ger’s base) were employed as halogen bond acceptors. The crystal structures of seven halogen-bonded complexes show C-X···Y (X = I, Br; Y = N, O) distances shorter than the sum of the van der Waals radii, and six of them contain the edge-to-edge C-H···X (X = I, Br) supramolecular hydrogen bond synthon. The stabilization energies with basis set superposition error correction of hydrogen bond synthons have been determined by DFT calculations, and they are in the range 2.9 to 5.7 kcalmol-1. To gain a deeper understanding of these interactions, noncovalent interaction methodology was also applied. Access copy available to the general public Unrestricted info:eu-repo/grantAgreement/ES/MEC/FPU14-06003 info:eu-repo/grantAgreement/ES/MINECO/MAT2012-38538-C03-01 info:eu-repo/grantAgreement/ES/MINECO/MAT2014-55205-P info:eu-repo/semantics/openAccess All rights reserved http://www.europeana.eu/rights/rr-f/ 3.972 2017 CRYSTALLOGRAPHY 6 / 26 = 0.231 2017 Q1 T1 MATERIALS SCIENCE, MULTIDISCIPLINARY 60 / 283 = 0.212 2017 Q1 T1 CHEMISTRY, MULTIDISCIPLINARY 46 / 169 = 0.272 2017 Q2 T1 1.154 2017 Chemistry (miscellaneous) 2017 Q1 Materials Science (miscellaneous) 2017 Q1 Condensed Matter Physics 2017 Q1 info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion Tejedor, Rosa María Universidad de Zaragoza (orcid)0000-0003-1141-5933 Royo, Eva Gaspar, Blanca Munárriz, Julen Universidad de Zaragoza (orcid)0000-0001-6089-6126 Chanthapally, Anjana Serrano, José Luis Universidad de Zaragoza (orcid)0000-0001-9866-6633 Vittal, Jagadese J. Uriel, Santiago Universidad de Zaragoza (orcid)0000-0001-7636-9187 2013 765 Universidad de Zaragoza Dpto. Química Orgánica Área Química Orgánica 2012 755 Universidad de Zaragoza Dpto. Química Física Área Química Física 17, 12 (2017), 6212-6223 Cryst. growth des. CRYSTAL GROWTH & DESIGN 1528-7483 966134 http://zaguan.unizar.es/record/145240/files/texto_completo.pdf Postprint 1194394 http://zaguan.unizar.es/record/145240/files/texto_completo.jpg?subformat=icon icon Postprint oai:zaguan.unizar.es:145240 articulos driver 2024-10-15-10:50:32 ARTICLE