in/out Isomerism of cyclophanes: a theoretical account of 2,6,15-trithia-[3(4,10)][7]metacyclophane and [3(4,10)][7]metacyclophane as well as their halogen substituted analogues
Само за регистроване кориснике
2017
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
A detailed theoretical investigation of cyclophanes with a divergent set of methods ranging from molecular mechanics through semiempirical to ab initio is presented. Cyclophanes have attracted interest over the years due to their unusual chemistry and increasing applications. There has been previous debate over the effects contributing to the greater stability of more-crowded in isomers of certain cyclophanes, and a higher strain in the out isomer was the prevailing explanation. Application of EDA-NOCV and SAPT analysis has enabled us to distinguish between different effects controlling isomer stability and determine the significance of all effects involved. Our results show that, although strain has a large significance, orbital stabilization within the molecule from the aromatic electron density is crucial. Furthermore, we analysed halogen-substituted cyclophanes in order to further understand these subtle effects.
Извор:
Physical Chemistry Chemical Physics, 2017, 19, 14, 9500-9508Издавач:
- Royal Soc Chemistry, Cambridge
Финансирање / пројекти:
- Рационални дизајн и синтеза биолошки активних и координационих једињења и функционалних материјала, релевантних у (био)нанотехнологији (RS-MESTD-Basic Research (BR or ON)-172035)
Напомена:
- The peer-reviewed version: http://cer.ihtm.bg.ac.rs/handle/123456789/2903
DOI: 10.1039/c7cp00557a
ISSN: 1463-9076
PubMed: 28338132
WoS: 000399164400018
Scopus: 2-s2.0-85019573956
Институција/група
IHTMTY - JOUR AU - Vujovic, Milena AU - Zlatar, Matija AU - Milčić, Miloš AU - Gruden, Maja PY - 2017 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2202 AB - A detailed theoretical investigation of cyclophanes with a divergent set of methods ranging from molecular mechanics through semiempirical to ab initio is presented. Cyclophanes have attracted interest over the years due to their unusual chemistry and increasing applications. There has been previous debate over the effects contributing to the greater stability of more-crowded in isomers of certain cyclophanes, and a higher strain in the out isomer was the prevailing explanation. Application of EDA-NOCV and SAPT analysis has enabled us to distinguish between different effects controlling isomer stability and determine the significance of all effects involved. Our results show that, although strain has a large significance, orbital stabilization within the molecule from the aromatic electron density is crucial. Furthermore, we analysed halogen-substituted cyclophanes in order to further understand these subtle effects. PB - Royal Soc Chemistry, Cambridge T2 - Physical Chemistry Chemical Physics T1 - in/out Isomerism of cyclophanes: a theoretical account of 2,6,15-trithia-[3(4,10)][7]metacyclophane and [3(4,10)][7]metacyclophane as well as their halogen substituted analogues VL - 19 IS - 14 SP - 9500 EP - 9508 DO - 10.1039/c7cp00557a ER -
@article{ author = "Vujovic, Milena and Zlatar, Matija and Milčić, Miloš and Gruden, Maja", year = "2017", abstract = "A detailed theoretical investigation of cyclophanes with a divergent set of methods ranging from molecular mechanics through semiempirical to ab initio is presented. Cyclophanes have attracted interest over the years due to their unusual chemistry and increasing applications. There has been previous debate over the effects contributing to the greater stability of more-crowded in isomers of certain cyclophanes, and a higher strain in the out isomer was the prevailing explanation. Application of EDA-NOCV and SAPT analysis has enabled us to distinguish between different effects controlling isomer stability and determine the significance of all effects involved. Our results show that, although strain has a large significance, orbital stabilization within the molecule from the aromatic electron density is crucial. Furthermore, we analysed halogen-substituted cyclophanes in order to further understand these subtle effects.", publisher = "Royal Soc Chemistry, Cambridge", journal = "Physical Chemistry Chemical Physics", title = "in/out Isomerism of cyclophanes: a theoretical account of 2,6,15-trithia-[3(4,10)][7]metacyclophane and [3(4,10)][7]metacyclophane as well as their halogen substituted analogues", volume = "19", number = "14", pages = "9500-9508", doi = "10.1039/c7cp00557a" }
Vujovic, M., Zlatar, M., Milčić, M.,& Gruden, M.. (2017). in/out Isomerism of cyclophanes: a theoretical account of 2,6,15-trithia-[3(4,10)][7]metacyclophane and [3(4,10)][7]metacyclophane as well as their halogen substituted analogues. in Physical Chemistry Chemical Physics Royal Soc Chemistry, Cambridge., 19(14), 9500-9508. https://doi.org/10.1039/c7cp00557a
Vujovic M, Zlatar M, Milčić M, Gruden M. in/out Isomerism of cyclophanes: a theoretical account of 2,6,15-trithia-[3(4,10)][7]metacyclophane and [3(4,10)][7]metacyclophane as well as their halogen substituted analogues. in Physical Chemistry Chemical Physics. 2017;19(14):9500-9508. doi:10.1039/c7cp00557a .
Vujovic, Milena, Zlatar, Matija, Milčić, Miloš, Gruden, Maja, "in/out Isomerism of cyclophanes: a theoretical account of 2,6,15-trithia-[3(4,10)][7]metacyclophane and [3(4,10)][7]metacyclophane as well as their halogen substituted analogues" in Physical Chemistry Chemical Physics, 19, no. 14 (2017):9500-9508, https://doi.org/10.1039/c7cp00557a . .