ACS Publications. Most Trusted. Most Cited. Most Read

OR SEARCH CITATIONS

My Activity
Recently Viewed
You have not visited any articles yet, Please visit some articles to see contents here.
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Phys. Chem. B 2008, 112, 4, 1184-1188
RETURN TO ISSUEPREVArticleNEXT

1,1-Dichloroethane:  A Molecular Crystal Structure without van der Waals Contacts?

View Author Information
Institute of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland, and Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland
Cite this: J. Phys. Chem. B 2008, 112, 4, 1184–1188
Publication Date (Web):January 9, 2008
https://doi.org/10.1021/jp075491p
Copyright © 2008 American Chemical Society
RIGHTS & PERMISSIONS
Article Views
256
Altmetric
-
Citations
24
LEARN ABOUT THESE METRICS
Read OnlinePDF (253 KB)
Get e-Alerts
Supporting Info (1)»
SUBJECTS:

Abstract

Isochoric and isobaric freezing of 1,1-dichloroethane, CH3CHCl2, mp = 176.19 K, yielded the orthorhombic structure, space group Pnma, with the fully ordered molecules, in the staggered conformation, located on mirror planes. The CH3CHCl2 ambient-pressure (0.1 MPa) structures were determined at 160 and 100 K, whereas the 295 K high-pressure structures were determined at 0.59 and 1.51 GPa. At 0.1 MPa, all intermolecular distances are considerably longer than the sums of the van der Waals radii, and only a pressure of about 1.5 GPa squeezed the Cl···Cl and Cl···H contacts to distances commensurate with these sums. The exceptionally large difference between the melting points of isomeric 1,1- and 1,2-dichloroethane can be rationalized in terms of their molecular-packing efficiency. It has been shown that the location of atoms in molecules affects their intermolecular interactions, and hence their van der Waals radii are the function of molecular structures.

†

 University of Opole.

‡

 Adam Mickiewicz University.

*

 To whom correspondence should be addressed. E-mail:  [email protected] amu.edu.pl.

Supporting Information Available

ARTICLE SECTIONS
Jump To

Crystallographic data in CIF format. This material is available free of charge via the Internet at http://pubs.acs.org.

Terms & Conditions

Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By

This article is cited by 24 publications.

  1. Maciej Bujak, Hans-Georg Stammler, Norbert W. Mitzel. Molecules Forced to Interact: Benzene and Pentafluoroiodobenzene. Crystal Growth & Design 2020, 20 (5) , 3217-3223. https://doi.org/10.1021/acs.cgd.0c00071
  2. Michał Kaźmierczak and Andrzej Katrusiak . Bimodal Distribution of the Shortest Intermolecular Contacts in Crystals of Organic Compounds. Crystal Growth & Design 2014, 14 (5) , 2223-2229. https://doi.org/10.1021/cg4018008
  3. Michał Kaźmierczak and Andrzej Katrusiak . The Most Loose Crystals of Organic Compounds. The Journal of Physical Chemistry C 2013, 117 (3) , 1441-1446. https://doi.org/10.1021/jp311403k
  4. Roman Gajda and Andrzej Katrusiak. Electrostatic Matching versus Close-Packing Molecular Arrangement in Compressed Dimethyl Sulfoxide (DMSO) Polymorphs. The Journal of Physical Chemistry B 2009, 113 (8) , 2436-2442. https://doi.org/10.1021/jp808987k
  5. Michał Kaźmierczak, Andrzej Katrusiak. The shortest chalcogen...halogen contacts in molecular crystals. Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 2019, 75 (5) , 865-869. https://doi.org/10.1107/S2052520619011004
  6. Maciej Bujak. Melting point, molecular symmetry and aggregation of tetrachlorobenzene isomers: the role of halogen bonding. Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 2018, 74 (5) , 458-466. https://doi.org/10.1107/S2052520618012295
  7. Maciej Bujak, Marcin Podsiadło, Andrzej Katrusiak. Loose crystals engineered by mismatched halogen bonds in hexachloroethane. CrystEngComm 2018, 20 (3) , 328-333. https://doi.org/10.1039/C7CE01980G
  8. Wenxue Li, Liping Chen, Yiwei Su, Hua Yin, Yaqin Pang, Zhixiong Zhuang. 1,2-Dichloroethane induced nephrotoxicity through ROS mediated apoptosis in vitro and in vivo. Toxicology Research 2015, 4 (5) , 1389-1399. https://doi.org/10.1039/C5TX00056D
  9. Kamil F. Dziubek, Andrzej Katrusiak. Structure–melting relations in isomeric dibromobenzenes. Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 2014, 70 (3) , 492-497. https://doi.org/10.1107/S2052520614011445
  10. Marcin Podsiadło, Maciej Bujak, Andrzej Katrusiak. Chemistry of density: extension and structural origin of Carnelley's rule in chloroethanes. CrystEngComm 2012, 14 (13) , 4496. https://doi.org/10.1039/c2ce25097g
  11. Mohammed A. H. Alamiry, Andrew C. Benniston, Graeme Copley, Anthony Harriman. Freezing and glass transition phenomena for 1,2-dichloroethane under high pressure as revealed by fluorescence spectroscopy. RSC Advances 2012, 2 (5) , 1936. https://doi.org/10.1039/c2ra00848c
  12. Maciej Bujak, Marcin Podsiadło, Andrzej Katrusiak. Crystalline gas of 1,1,1-trichloroethane. CrystEngComm 2011, 13 (2) , 396-398. https://doi.org/10.1039/C0CE00493F
  13. Andrzej Katrusiak, Marcin Podsiadło, Armand Budzianowski. Association CH···π and No van der Waals Contacts at the Lowest Limits of Crystalline Benzene I and II Stability Regions. Crystal Growth & Design 2010, 10 (8) , 3461-3465. https://doi.org/10.1021/cg1002594
  14. Maciej Bujak, Andrzej Katrusiak. Molecular association in low-temperature and high-pressure polymorphs of 1,1,1,2-tetrachloroethane. CrystEngComm 2010, 12 (4) , 1263-1268. https://doi.org/10.1039/B918360D
  15. Anna Olejniczak, Andrzej Katrusiak, Pierangelo Metrangolo, Giuseppe Resnati. Molecular association in 2-bromo-2-chloro-1,1,1-trifluoroethane (Halothane). Journal of Fluorine Chemistry 2009, 130 (2) , 248-253. https://doi.org/10.1016/j.jfluchem.2008.10.009
  16. Anna Olejniczak, Andrzej Katrusiak, Ashwani Vij. Weak intermolecular interactions and molecular aggregation in isostructural dihaloperfluoroethanes,. CrystEngComm 2009, 11 (6) , 1073. https://doi.org/10.1039/b819942f
  17. Marcin Podsiadło, Andrzej Katrusiak. Electrostatic matching in phase IV of chloroiodomethane: a new aggregation pattern in the isostructural classes of dihalomethanes. CrystEngComm 2009, 11 (7) , 1391. https://doi.org/10.1039/b820422e
  18. Anna Olejniczak, Andrzej Katrusiak, Ashwani Vij. Halogen⋯oxygen aggregation and disorder modes in pressure frozen XCF2CF2X : 1,4-dioxane (X = Br,I) complexes. CrystEngComm 2009, 11 (7) , 1240. https://doi.org/10.1039/b822832a
  19. Z. Dega-Szafran, A. Katrusiak, M. Szafran. Molecular structure of 1:1 complex of 1,4-dimethylpiperazine di-betaine with l-tartaric acid studied by X-ray diffraction, FTIR, Raman and NMR spectroscopy and DFT calculations. Journal of Molecular Structure 2008, 891 (1-3) , 258-265. https://doi.org/10.1016/j.molstruc.2008.03.057
  20. Adam Huczyński, Izabela Paluch, Małgorzata Ratajczak-Sitarz, Andrzej Katrusiak, Joanna Stefańska, Bogumil Brzezinski, Franz Bartl. Spectroscopic studies, crystal structures and antimicrobial activities of a new lasalocid 1-naphthylmethyl ester. Journal of Molecular Structure 2008, 891 (1-3) , 481-490. https://doi.org/10.1016/j.molstruc.2008.04.037
  21. A. Komasa, A. Katrusiak, M. Szafran, P. Barczyński, Z. Dega-Szafran. Molecular structure, hydrogen bonding and spectroscopic properties of the complex of piperidine-4-carboxylic acid with chloroacetic acid. Journal of Molecular Structure 2008, 889 (1-3) , 112-118. https://doi.org/10.1016/j.molstruc.2008.01.038
  22. Roman Gajda, Andrzej Katrusiak. Pressure-freezing with conformational conversion of 3-aminopropan-1-ol molecules. Acta Crystallographica Section B Structural Science 2008, 64 (4) , 476-482. https://doi.org/10.1107/S0108768108012779
  23. Marcin Podsiadło, Andrzej Katrusiak. Isostructural relations in dihalomethanes and disproportionation of bromoiodomethane. CrystEngComm 2008, 10 (10) , 1436. https://doi.org/10.1039/b805065a
  24. Maciej Bujak, Marcin Podsiadło, Andrzej Katrusiak. Energetics of conformational conversion between 1,1,2-trichloroethane polymorphs. Chemical Communications 2008, 1595 (37) , 4439. https://doi.org/10.1039/b807372d

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE