Short Intramolecular O···O Contact in Some o-Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area
Само за регистроване кориснике
2018
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Statistical analysis of data extracted from the Cambridge Structural Database (CSD) has been used to investigate the crystal structure properties of odialkoxybenzene derivatives, compounds containing two ether oxygen acceptors in ortho positions of benzene ring. It has been shown that in more than 90% of cases, the fragment has predictable geometrical characteristics where the two ether oxygens form short interatomic O center dot center dot center dot O contact (2.57 A in average), while O-substitutents take trans position, both approximately coplanar with the benzene ring. Such arrangement of oxygen acceptors produces a large and uniform area of the negative electrostatic potential suitable for multiple hydrogen bonding. The acceptor abilities of the O center dot center dot center dot O system have been investigated by the statistical CSD analysis. The ab initio estimation of the interaction energy in the dimer of o-dimethoxybenzene (DMB) and H2O, employed as a model system, is achiev...ed via high-level electron correlation CCSD(T) calculation with the complete basis set extrapolation. The interaction energy is estimated to be 6.5 kcal/mol. The results indicate the existence of a very flat potential the region between methoxy oxygens and that DMB water is a highly flexible system. The structural role of the O center dot center dot center dot O acceptor system is particularly interesting considering its ability to form multiple hydrogen bonding
Извор:
Crystal Growth & Design, 2018, 18, 3, 1303-1314Издавач:
- American Chemical Society (ACS)
Финансирање / пројекти:
- Дизајнирање, синтеза, карактеризација и процена практичне примене координационих и органометалних једињења (RS-172014)
- Рационални дизајн и синтеза биолошки активних и координационих једињења и функционалних материјала, релевантних у (био)нанотехнологији (RS-172035)
- Проучавање физичкохемијских и биохемијских процеса у животној средини који утичу на загађење и истраживање могућности за минимизирање последица (RS-172001)
- Моделирање и нумеричке симулације сложених вишечестичних система (RS-171017)
- Gaussian program - 1720035
Напомена:
- The peer-reviewed version: https://cer.ihtm.bg.ac.rs/handle/123456789/4283
- The supplementary information: https://cer.ihtm.bg.ac.rs/handle/123456789/4479
Повезане информације:
- Друга верзија
https://cer.ihtm.bg.ac.rs/handle/123456789/4283 - Повезани садржај
https://cer.ihtm.bg.ac.rs/handle/123456789/4479
DOI: 10.1021/acs.cgd.7b00914
ISSN: 1528-7483
WoS: 000427203700009
Scopus: 2-s2.0-85043277655
Институција/група
IHTMTY - JOUR AU - Bogdanović, Goran A. AU - Ostojić, Bojana AU - Novakovic, Sladjana B. PY - 2018 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2322 AB - Statistical analysis of data extracted from the Cambridge Structural Database (CSD) has been used to investigate the crystal structure properties of odialkoxybenzene derivatives, compounds containing two ether oxygen acceptors in ortho positions of benzene ring. It has been shown that in more than 90% of cases, the fragment has predictable geometrical characteristics where the two ether oxygens form short interatomic O center dot center dot center dot O contact (2.57 A in average), while O-substitutents take trans position, both approximately coplanar with the benzene ring. Such arrangement of oxygen acceptors produces a large and uniform area of the negative electrostatic potential suitable for multiple hydrogen bonding. The acceptor abilities of the O center dot center dot center dot O system have been investigated by the statistical CSD analysis. The ab initio estimation of the interaction energy in the dimer of o-dimethoxybenzene (DMB) and H2O, employed as a model system, is achieved via high-level electron correlation CCSD(T) calculation with the complete basis set extrapolation. The interaction energy is estimated to be 6.5 kcal/mol. The results indicate the existence of a very flat potential the region between methoxy oxygens and that DMB water is a highly flexible system. The structural role of the O center dot center dot center dot O acceptor system is particularly interesting considering its ability to form multiple hydrogen bonding PB - American Chemical Society (ACS) T2 - Crystal Growth & Design T1 - Short Intramolecular O···O Contact in Some o-Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area VL - 18 IS - 3 SP - 1303 EP - 1314 DO - 10.1021/acs.cgd.7b00914 ER -
@article{ author = "Bogdanović, Goran A. and Ostojić, Bojana and Novakovic, Sladjana B.", year = "2018", abstract = "Statistical analysis of data extracted from the Cambridge Structural Database (CSD) has been used to investigate the crystal structure properties of odialkoxybenzene derivatives, compounds containing two ether oxygen acceptors in ortho positions of benzene ring. It has been shown that in more than 90% of cases, the fragment has predictable geometrical characteristics where the two ether oxygens form short interatomic O center dot center dot center dot O contact (2.57 A in average), while O-substitutents take trans position, both approximately coplanar with the benzene ring. Such arrangement of oxygen acceptors produces a large and uniform area of the negative electrostatic potential suitable for multiple hydrogen bonding. The acceptor abilities of the O center dot center dot center dot O system have been investigated by the statistical CSD analysis. The ab initio estimation of the interaction energy in the dimer of o-dimethoxybenzene (DMB) and H2O, employed as a model system, is achieved via high-level electron correlation CCSD(T) calculation with the complete basis set extrapolation. The interaction energy is estimated to be 6.5 kcal/mol. The results indicate the existence of a very flat potential the region between methoxy oxygens and that DMB water is a highly flexible system. The structural role of the O center dot center dot center dot O acceptor system is particularly interesting considering its ability to form multiple hydrogen bonding", publisher = "American Chemical Society (ACS)", journal = "Crystal Growth & Design", title = "Short Intramolecular O···O Contact in Some o-Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area", volume = "18", number = "3", pages = "1303-1314", doi = "10.1021/acs.cgd.7b00914" }
Bogdanović, G. A., Ostojić, B.,& Novakovic, S. B.. (2018). Short Intramolecular O···O Contact in Some o-Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area. in Crystal Growth & Design American Chemical Society (ACS)., 18(3), 1303-1314. https://doi.org/10.1021/acs.cgd.7b00914
Bogdanović GA, Ostojić B, Novakovic SB. Short Intramolecular O···O Contact in Some o-Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area. in Crystal Growth & Design. 2018;18(3):1303-1314. doi:10.1021/acs.cgd.7b00914 .
Bogdanović, Goran A., Ostojić, Bojana, Novakovic, Sladjana B., "Short Intramolecular O···O Contact in Some o-Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area" in Crystal Growth & Design, 18, no. 3 (2018):1303-1314, https://doi.org/10.1021/acs.cgd.7b00914 . .