Influence of methoxy-substituents on the strength of Br  …  Br type II halogen bonds in bromobenzoic acid

Raffo, Pablo Alejandro; Marcolongo, Juan P.; Funes, Alejandro V.; Slep, Leonardo D.; Baggio, Ricardo; Cukiernik, Fabio Daniel

doi:10.1016/j.molstruc.2015.12.016

Cited by 2 publications

(4 citation statements)

References 41 publications

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“…5 and 6). This type of contact has already been observed in halogenated aromatic compounds as Br-benzamide (Tothadi et al, 2013), Br-benzoic acids (Ohkura et al, 1972;Raffo et al, 2016), etc. In the present case, the effect is that of 'threading' parallel columns into a strongly bound 'bi-columnar' unit.…”

Section: Figuresupporting

confidence: 54%

“…Periodic calculations were carried out with the CRYSTAL14 package (Dovesi et al, 2014) using the B3LYP hybrid functional, 6-31G** or TZVP (Peintinger et al, 2012) basis sets for C and F atoms, and the Doll's (Doll & Stoll, 1998) or HAYWLC (Prencipe, 1990) basis sets for I atoms. The basis set 6-31G** proved adequate for exploring other related systems exhibiting halogen bonds (Ellman, 2006;Raffo et al, 2016;Rosokha et al, 2013) and was found to yield cohesion energies very similar to those obtained through the use of other basis sets like TZP (Civalleri et al, 2008). With I atoms, bigger basis sets were required, so the Doll's (Pham et al, 2014) or HAYWLC basis sets were used.…”

Section: Computational Calculationsmentioning

confidence: 99%

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Polymorphism of a widely used building block for halogen-bonded assemblies: 1,3,5-trifluoro-2,4,6-triiodobenzene

et al. 2017

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After reporting the structure of a new polymorph of 1,3,5-trifluoro-2,4,6-triiodobenzene (denoted BzF3I3), CFI, (I), which crystallized in the space group P2/c, we perform a comparative analysis with the already reported P2/n polymorph, (II) [Reddy et al. (2006). Chem. Eur. J. 12, 2222-2234]. In polymorph (II), type-II I...I halogen bonds and I...π interactions connect molecules in such a way that a three-dimensional structure is formed; however, the way in which molecules are connected in polymorph (I), through type-II I...I halogen bonds and π-π interactions, gives rise to an exfoldable lamellar structure, which looks less tightly bound than that of (II). In agreement with this structural observation, both the melting point and the melting enthalpy of (I) are lower than those of (II).

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Section: Figuresupporting

confidence: 54%

Section: Computational Calculationsmentioning

confidence: 99%

Polymorphism of a widely used building block for halogen-bonded assemblies: 1,3,5-trifluoro-2,4,6-triiodobenzene

et al. 2017

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“…5, for example) and the negative charge density on the 'belt' on the other 'perpendicular' Br atom (Br2 ii on Fig. 5), although very small covalent components have also been discerned in some cases (Cavallo et al, 2016;Raffo et al, 2016;Capdevila-Cortada & Novoa, 2015).…”

Section: Resultsmentioning

confidence: 98%

“…Quantum-mechanical calculations on the complexes included in this study were performed at the M062X/6-311++G(d,p) level of theory using the crystallographic coordinates (single-point calculations) within the GAUSSIAN09 program (Frisch et al, 2009). This functional/basis set combi-nation has proven to be adequate to explore other related systems exhibiting halogen bonds (Raffo et al, 2016;Rosokha et al, 2013). The basis set superposition error for the calculation of interaction energies was corrected using the counterpoise method.…”

Section: Programs Used and Approximations Performedmentioning

confidence: 99%

Br...Br and van der Waals interactions along a homologous series: crystal packing of 1,2-dibromo-4,5-dialkoxybenzenes

Suárez

Müller

Suburu

et al. 2016

Acta Crystallogr Sect B

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The crystalline structures of four homologues of the 1,2-dibromo-4,5-dialkoxybenzene series [BrCH(OCH) for n = 2, 12, 14 and 18] have been solved by means of single-crystal crystallography. Comparison along the series, including the previously reported n = 10 and n = 16 derivatives, shows a clear metric trend (b and c essentially fixed along the series and a growing linearly with n), in spite of some subtle differences in space groups and/or packing modes. A uniform packing pattern for the aliphatic chains has been found for the n = 12 to 18 homologues, which slightly differs from that of the n = 10 derivative. The crystalline structures of all the higher homologues (n = 10-18) seem to arise from van der Waals interchain interactions and, to a lesser extent, type II Br...Br interactions. The dominant role of interchain interactions provides direct structural support for the usual interpretation of melting point trends like that found along this series. Atoms in Molecules (AIM) analysis allows a comparison of the relative magnitude of the interchain and Br...Br interactions, an analysis validated by the measured melting enthalpies.

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Influence of methoxy-substituents on the strength of Br … Br type II halogen bonds in bromobenzoic acid

Cited by 2 publications

References 41 publications

Polymorphism of a widely used building block for halogen-bonded assemblies: 1,3,5-trifluoro-2,4,6-triiodobenzene

Polymorphism of a widely used building block for halogen-bonded assemblies: 1,3,5-trifluoro-2,4,6-triiodobenzene

Br...Br and van der Waals interactions along a homologous series: crystal packing of 1,2-dibromo-4,5-dialkoxybenzenes

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