Crystal Structure Survey and Theoretical Analysis of Bifurcated Halogen Bonds.
Journal
Crystal growth & design
ISSN: 1528-7483
Titre abrégé: Cryst Growth Des
Pays: United States
ID NLM: 101261892
Informations de publication
Date de publication:
02 Nov 2022
02 Nov 2022
Historique:
received:
28
06
2022
revised:
26
09
2022
entrez:
8
11
2022
pubmed:
9
11
2022
medline:
9
11
2022
Statut:
ppublish
Résumé
The possibility that two Lewis bases can share a single halogen atom within the context of a bifurcated halogen bond (XB) is explored first by a detailed examination of the CSD. Of the more than 22,000 geometries that fit the definition of an XB (with X = Cl, Br, I), less than 2% are bifurcated. There is a heavy weighting of I in such bifurcated arrangements as opposed to Br, which prefers monofurcated bonds. The conversion from mono to bifurcated is associated with a smaller number of short contact distances, as well as a trend toward lesser linearity. The two XBs within a bifurcated system are somewhat symmetrical: the two lengths generally differ by less than 0.05 Å, and the two XB angles are within several degrees of one another. Quantum calculations of model systems reflect the patterns observed in crystals and reinforce the idea that the negative cooperativity within a bifurcated XB weakens and lengthens each individual bond.
Identifiants
pubmed: 36345386
doi: 10.1021/acs.cgd.2c00726
pmc: PMC9634799
doi:
Types de publication
Journal Article
Langues
eng
Pagination
6521-6530Informations de copyright
© 2022 The Authors. Published by American Chemical Society.
Déclaration de conflit d'intérêts
The authors declare no competing financial interest.
Références
Phys Chem Chem Phys. 2021 Jun 30;23(25):13853-13861
pubmed: 34156052
Molecules. 2019 Sep 12;24(18):
pubmed: 31547416
Phys Chem Chem Phys. 2016 Mar 14;18(10):7300-9
pubmed: 26900007
ACS Chem Biol. 2020 Jul 17;15(7):1942-1948
pubmed: 32469201
Chem Soc Rev. 2022 Feb 21;51(4):1454-1469
pubmed: 35103265
Phys Chem Chem Phys. 2015 Mar 7;17(9):6440-50
pubmed: 25656525
Molecules. 2021 Jan 12;26(2):
pubmed: 33445461
Chempluschem. 2021 Aug;86(8):1123-1127
pubmed: 34402218
J Phys Chem B. 2010 Jun 24;114(24):8278-83
pubmed: 20509699
J Mol Model. 2007 Feb;13(2):291-6
pubmed: 16927107
Phys Chem Chem Phys. 2005 Sep 21;7(18):3297-305
pubmed: 16240044
Phys Chem Chem Phys. 2006 Mar 7;8(9):1057-65
pubmed: 16633586
J Am Chem Soc. 2015 Jan 28;137(3):1008-11
pubmed: 25578373
Chemphyschem. 2004 Nov 12;5(11):1779-82
pubmed: 15580940
J Phys Chem A. 2012 Feb 23;116(7):1838-45
pubmed: 22273113
Phys Chem Chem Phys. 2017 Jun 14;19(23):15530-15540
pubmed: 28581553
Dalton Trans. 2013 Jun 28;42(24):8617-36
pubmed: 23632803
Angew Chem Int Ed Engl. 1999 Sep;38(18):2686-2714
pubmed: 10508357
Chemistry. 2016 Dec 23;22(52):18850-18858
pubmed: 27740702
J Chem Theory Comput. 2009 Jan 13;5(1):155-63
pubmed: 26609829
Acta Crystallogr B Struct Sci Cryst Eng Mater. 2016 Apr;72(Pt 2):171-9
pubmed: 27048719
Chem Commun (Camb). 2016 Apr 25;52(32):5565-8
pubmed: 27020251
Angew Chem Int Ed Engl. 2015 Sep 28;54(40):11711-5
pubmed: 26276699
J Mol Model. 2007 Feb;13(2):305-11
pubmed: 17013631
Phys Chem Chem Phys. 2015 Jun 21;17(23):15226-35
pubmed: 25993543
Molecules. 2021 Aug 26;26(17):
pubmed: 34500610
Phys Chem Chem Phys. 2020 Mar 18;22(11):6122-6130
pubmed: 32124890
Proc Natl Acad Sci U S A. 1975 Jul;72(7):2606-10
pubmed: 1058476
Phys Chem Chem Phys. 2017 May 24;19(20):12936-12941
pubmed: 28480457
Phys Chem Chem Phys. 2016 Feb 7;18(5):3581-90
pubmed: 26750543