Phenol and Toluene Stacking Interactions, including Interactions at Large Horizontal Displacements. Study of Crystal Structures and Calculation of Potential Energy Surfaces
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2020
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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.
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Crystal Growth and Design, 2020, 20, 1025-1034Publisher:
- American Chemical Society (ACS)
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DOI: 10.1021/acs.cgd.9b01353
ISSN: 1528-7483
WoS: 000512216600056
Scopus: 2-s2.0-85078231622
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IHTMTY - 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 . .