CER - Central Repository
Institute of Chemistry, Technology and Metallurgy
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrillic)
    • Serbian (Latin)
  • Login
View Item 
  •   CER
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
  •   CER
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

Phenol and Toluene Stacking Interactions, including Interactions at Large Horizontal Displacements. Study of Crystal Structures and Calculation of Potential Energy Surfaces

Authorized Users Only
2020
Authors
Živković, Jelena M.
Stanković, Ivana
Ninković, Dragan B.
Zarić, Snežana D.
Article (Published version)
,
American Chemical Society (ACS)
Metadata
Show full item record
Abstract
The study of crystal structures from the Cambridge Structural Database (CSD) shows that most of p-phenol/p-phenol and toluene/toluene stacking interactions are at large horizontal displacements (offsets) as well as benzene/benzene interactions. The interactions at large horizontal displacements are stabilized by the addition of simultaneous interactions in supramolecular structures in crystals. The stacking p-phenol/p-phenol tends to be orientated in a parallel and antiparallel fashion, while stacking toluene/toluene is almost all in an antiparallel orientation. It is in accordance with calculated interaction energies. Namely, the strongest interaction energies for parallel and antiparallel phenol/phenol dimers are -5.12 and -4.40 kcal/mol, at offsets of 1.5 and 3.0 Å, respectively, while for parallel and antiparallel toluene/toluene dimers, energies are -3.98 and -5.39 kcal/mol, at offsets of 3.0 Å. These interactions are stronger than benzene/benzene stacking (-2.85 kcal/mol), as a c...onsequence of the presence of the substituents. Similar to benzene/benzene stacking, interactions for phenol/phenol and toluene/toluene stacking at large offsets (4.0 Å) can be strong, stronger than -2.0 kcal/mol.

Source:
Crystal Growth and Design, 2020, 20, 1025-1034
Publisher:
  • American Chemical Society (ACS)
Funding / projects:
  • Noncovalent interactions of pi-systems and their role in molecular recognition (RS-172065)

DOI: 10.1021/acs.cgd.9b01353

ISSN: 1528-7483

WoS: 000512216600056

Scopus: 2-s2.0-85078231622
[ Google Scholar ]
14
7
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/3395
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Živković, Jelena M.
AU  - Stanković, Ivana
AU  - Ninković, Dragan B.
AU  - Zarić, Snežana D.
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3395
AB  - The study of crystal structures from the Cambridge Structural Database (CSD) shows that most of p-phenol/p-phenol and toluene/toluene stacking interactions are at large horizontal displacements (offsets) as well as benzene/benzene interactions. The interactions at large horizontal displacements are stabilized by the addition of simultaneous interactions in supramolecular structures in crystals. The stacking p-phenol/p-phenol tends to be orientated in a parallel and antiparallel fashion, while stacking toluene/toluene is almost all in an antiparallel orientation. It is in accordance with calculated interaction energies. Namely, the strongest interaction energies for parallel and antiparallel phenol/phenol dimers are -5.12 and -4.40 kcal/mol, at offsets of 1.5 and 3.0 Å, respectively, while for parallel and antiparallel toluene/toluene dimers, energies are -3.98 and -5.39 kcal/mol, at offsets of 3.0 Å. These interactions are stronger than benzene/benzene stacking (-2.85 kcal/mol), as a consequence of the presence of the substituents. Similar to benzene/benzene stacking, interactions for phenol/phenol and toluene/toluene stacking at large offsets (4.0 Å) can be strong, stronger than -2.0 kcal/mol.
PB  - American Chemical Society (ACS)
T2  - Crystal Growth and Design
T1  - Phenol and Toluene Stacking Interactions, including Interactions at Large Horizontal Displacements. Study of Crystal Structures and Calculation of Potential Energy Surfaces
VL  - 20
SP  - 1025
EP  - 1034
DO  - 10.1021/acs.cgd.9b01353
ER  - 
@article{
author = "Živković, Jelena M. and Stanković, Ivana and Ninković, Dragan B. and Zarić, Snežana D.",
year = "2020",
abstract = "The study of crystal structures from the Cambridge Structural Database (CSD) shows that most of p-phenol/p-phenol and toluene/toluene stacking interactions are at large horizontal displacements (offsets) as well as benzene/benzene interactions. The interactions at large horizontal displacements are stabilized by the addition of simultaneous interactions in supramolecular structures in crystals. The stacking p-phenol/p-phenol tends to be orientated in a parallel and antiparallel fashion, while stacking toluene/toluene is almost all in an antiparallel orientation. It is in accordance with calculated interaction energies. Namely, the strongest interaction energies for parallel and antiparallel phenol/phenol dimers are -5.12 and -4.40 kcal/mol, at offsets of 1.5 and 3.0 Å, respectively, while for parallel and antiparallel toluene/toluene dimers, energies are -3.98 and -5.39 kcal/mol, at offsets of 3.0 Å. These interactions are stronger than benzene/benzene stacking (-2.85 kcal/mol), as a consequence of the presence of the substituents. Similar to benzene/benzene stacking, interactions for phenol/phenol and toluene/toluene stacking at large offsets (4.0 Å) can be strong, stronger than -2.0 kcal/mol.",
publisher = "American Chemical Society (ACS)",
journal = "Crystal Growth and Design",
title = "Phenol and Toluene Stacking Interactions, including Interactions at Large Horizontal Displacements. Study of Crystal Structures and Calculation of Potential Energy Surfaces",
volume = "20",
pages = "1025-1034",
doi = "10.1021/acs.cgd.9b01353"
}
Živković, J. M., Stanković, I., Ninković, D. B.,& Zarić, S. D.. (2020). Phenol and Toluene Stacking Interactions, including Interactions at Large Horizontal Displacements. Study of Crystal Structures and Calculation of Potential Energy Surfaces. in Crystal Growth and Design
American Chemical Society (ACS)., 20, 1025-1034.
https://doi.org/10.1021/acs.cgd.9b01353
Živković JM, Stanković I, Ninković DB, Zarić SD. Phenol and Toluene Stacking Interactions, including Interactions at Large Horizontal Displacements. Study of Crystal Structures and Calculation of Potential Energy Surfaces. in Crystal Growth and Design. 2020;20:1025-1034.
doi:10.1021/acs.cgd.9b01353 .
Živković, Jelena M., Stanković, Ivana, Ninković, Dragan B., Zarić, Snežana D., "Phenol and Toluene Stacking Interactions, including Interactions at Large Horizontal Displacements. Study of Crystal Structures and Calculation of Potential Energy Surfaces" in Crystal Growth and Design, 20 (2020):1025-1034,
https://doi.org/10.1021/acs.cgd.9b01353 . .

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

re3dataOpenAIRERCUB
 

 

All of DSpaceInstitutions/communitiesAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

re3dataOpenAIRERCUB