Next Article in Journal
Microgreens—A Comprehensive Review of Bioactive Molecules and Health Benefits
Next Article in Special Issue
Interaction of Vinyl-Type Carbocations, C3H5+ and C4H7+ with Molecules of Water, Alcohols, and Acetone
Previous Article in Journal
Aspects of Applied Chemistry Related to Future Goals of Safety and Efficiency in Materials Development for Nuclear Energy
Previous Article in Special Issue
The Halogen Bond in Weakly Bonded Complexes and the Consequences for Aromaticity and Spin-Orbit Coupling
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molecules
Volume 28
Issue 2
10.3390/molecules28020875
molecules-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Article

How the Position of Substitution Affects Intermolecular Bonding in Halogen Derivatives of Carboranes: Crystal Structures of 1,2,3- and 8,9,12-Triiodo- and 8,9,12-Tribromo ortho-Carboranes

by
Kyrill Yu. Suponitsky
1,2,
Sergey A. Anufriev
1 and
Igor B. Sivaev
1,2,*
1
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., Moscow 119334, Russia
2
Basic Department of Chemistry of Innovative Materials and Technologies, G.V. Plekhanov Russian University of Economics, 36 Stremyannyi Line, Moscow 117997, Russia
*
Author to whom correspondence should be addressed.
Molecules 2023, 28(2), 875; https://doi.org/10.3390/molecules28020875
Submission received: 31 October 2022 / Revised: 10 January 2023 / Accepted: 12 January 2023 / Published: 15 January 2023
(This article belongs to the Special Issue Chemical Bond and Intermolecular Interactions)
Browse Figures
Versions Notes

Abstract

The crystal structures of two isomeric triiodo derivatives of ortho-carborane containing substituents in the three most electron-withdrawing positions of the carborane cage, 1,2,3-I3-1,2-C2B10H9, and the three most electron-donating positions, 8,9,12-I3-1,2-C2B10H9, as well as the crystal structure of 8,9,12-Br3-1,2-C2B10H9, were determined by single-crystal X-ray diffraction. In the structure of 1,2,3-I3-1,2-C2B10H9, an iodine atom attached to the boron atom (position 3) donates its lone pairs simultaneously to the σ-holes of both iodine atoms attached to the carbon atoms (positions 1 and 2) with the I⋯I distance of 3.554(2) Å and the C-I⋯I and B-I⋯I angles of 169.2(2)° and 92.2(2)°, respectively. The structure is additionally stabilized by a few B-H⋯I-shortened contacts. In the structure of 8,9,12-I3-1,2-C2B10H9, the I⋯I contacts of type II are very weak (the I⋯I distance is 4.268(4) Å, the B8-I8⋯I12 and B12-I12⋯I8 angles are 130.2(3)° and 92.2(3)°) and can only be regarded as dihalogen bonds formally. In comparison with the latter, the structure of 8,9,12-Br3-1,2-C2B10H9 demonstrates both similarities and differences. No Br⋯Br contacts of type II are observed, while there are two Br⋯Br halogen bonds of type I.
Keywords: ortho-carborane; iodo derivatives; X-ray structure; I⋯I dihalogen bond ortho-carborane; iodo derivatives; X-ray structure; I⋯I dihalogen bond
Graphical Abstract

Share and Cite

MDPI and ACS Style

Suponitsky, K.Y.; Anufriev, S.A.; Sivaev, I.B. How the Position of Substitution Affects Intermolecular Bonding in Halogen Derivatives of Carboranes: Crystal Structures of 1,2,3- and 8,9,12-Triiodo- and 8,9,12-Tribromo ortho-Carboranes. Molecules 2023, 28, 875. https://doi.org/10.3390/molecules28020875

AMA Style

Suponitsky KY, Anufriev SA, Sivaev IB. How the Position of Substitution Affects Intermolecular Bonding in Halogen Derivatives of Carboranes: Crystal Structures of 1,2,3- and 8,9,12-Triiodo- and 8,9,12-Tribromo ortho-Carboranes. Molecules. 2023; 28(2):875. https://doi.org/10.3390/molecules28020875

Chicago/Turabian Style

Suponitsky, Kyrill Yu., Sergey A. Anufriev, and Igor B. Sivaev. 2023. "How the Position of Substitution Affects Intermolecular Bonding in Halogen Derivatives of Carboranes: Crystal Structures of 1,2,3- and 8,9,12-Triiodo- and 8,9,12-Tribromo ortho-Carboranes" Molecules 28, no. 2: 875. https://doi.org/10.3390/molecules28020875

APA Style

Suponitsky, K. Y., Anufriev, S. A., & Sivaev, I. B. (2023). How the Position of Substitution Affects Intermolecular Bonding in Halogen Derivatives of Carboranes: Crystal Structures of 1,2,3- and 8,9,12-Triiodo- and 8,9,12-Tribromo ortho-Carboranes. Molecules, 28(2), 875. https://doi.org/10.3390/molecules28020875

Article Metrics

Back to TopTop