Inorganic benzenes as the noncovalent interaction donor: a study of the π-hole interactions
Tóm tắt
For inorganic benzenes C3N3X3 and B3O3X3 (X = H, F, CN), the positive electrostatic potentials (π-hole) were discovered above and below the inorganic benzene ring center. Then, the π-hole interactions between the inorganic benzenes and NCH have been designed and investigated by MP2/aug-cc-pVDZ calculations. In this paper, the termolecular complexes B3O3X3···NCH···NCH, C3N3X3···NCH···NCH (X = H, F, CN) were also designed to illustrate the enhancing effects of the H···N hydrogen bond on the π-hole interactions. The π-hole interaction energy was influenced by the strength of different electron-withdrawing substituents of inorganic benzenes, gradually increasing in the order of X = H, F, CN. What’s more, the π electron densities account for 71~88% of the total electron densities, indicating the strength of interaction energy is mainly determined by π-type electron densities.
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citation_journal_title=Chem Rev; citation_author=K Müller-Dethlefs, P Hobza; citation_volume=100; citation_publication_date=2000; citation_pages=143-167; citation_doi=10.1021/cr9900331; citation_id=CR1
citation_journal_title=Chem Rev; citation_author=G Cavallo, P Metrangolo, R Milani, T Pilati, A Priimagi, G Resnati, G Terraneo; citation_volume=116; citation_publication_date=2016; citation_pages=2478-2601; citation_doi=10.1021/acs.chemrev.5b00484; citation_id=CR2
citation_journal_title=Proc Natl Acad Sci U S A; citation_author=P Auffinger, FA Hays, E Westhof, PS Ho; citation_volume=101; citation_publication_date=2004; citation_pages=16789-16794; citation_doi=10.1073/pnas.0407607101; citation_id=CR3
citation_journal_title=Acta Crystallogr; citation_author=P Metrangolo, G Resnati, T Pilati, S Biella; citation_volume=61; citation_publication_date=2007; citation_pages=105-136; citation_id=CR4
citation_journal_title=J Mol Model; citation_author=T Clark, M Hennemann, JS Murray, P Politzer; citation_volume=13; citation_publication_date=2007; citation_pages=291-296; citation_doi=10.1007/s00894-006-0130-2; citation_id=CR5
citation_journal_title=Chem Rev; citation_author=H Wang, W Wang, WJ Jin; citation_volume=116; citation_publication_date=2016; citation_pages=5072-5104; citation_doi=10.1021/acs.chemrev.5b00527; citation_id=CR6
citation_journal_title=J Mol Model; citation_author=JS Murray, MC Concha, P Lane, P Hobza, P Politzer; citation_volume=14; citation_publication_date=2008; citation_pages=699-704; citation_doi=10.1007/s00894-008-0307-y; citation_id=CR7
citation_journal_title=Int J Quantum Chem; citation_author=JS Murray, P Lane, P Politzer; citation_volume=107; citation_publication_date=2007; citation_pages=2286-2292; citation_doi=10.1002/qua.21352; citation_id=CR8
citation_journal_title=J Mol Model; citation_author=JS Murray, P Lane, T Clark, KE Riley, P Politzer; citation_volume=18; citation_publication_date=2012; citation_pages=541-548; citation_doi=10.1007/s00894-011-1089-1; citation_id=CR9
citation_journal_title=Struct Chem; citation_author=T Lang, X Li, L Meng, S Zheng, Y Zeng; citation_volume=26; citation_publication_date=2014; citation_pages=213-221; citation_doi=10.1007/s11224-014-0486-3; citation_id=CR10
citation_journal_title=J Comput Sci; citation_author=JS Murray, ZP Shields, PG Seybold, P Politzer; citation_volume=10; citation_publication_date=2015; citation_pages=209-216; citation_doi=10.1016/j.jocs.2015.02.001; citation_id=CR11
citation_journal_title=Phys Chem Chem Phys; citation_author=P Politzer, JS Murray, T Clark; citation_volume=12; citation_publication_date=2010; citation_pages=7748-7757; citation_doi=10.1039/c004189k; citation_id=CR12
Politzer P, Murray JS (2017) J Comput Chem.
https://doi.org/10.1002/jcc.24891
citation_journal_title=ChemPhysChem; citation_author=Y Zeng, X Zhang, X Li, L Meng, S Zheng; citation_volume=12; citation_publication_date=2011; citation_pages=1080-1087; citation_doi=10.1002/cphc.201100008; citation_id=CR14
citation_journal_title=Aust J Chem; citation_author=SCAH Pierrefixe, FM Bickelhaupt; citation_volume=61; citation_publication_date=2008; citation_pages=209-215; citation_doi=10.1071/CH08043; citation_id=CR15
citation_journal_title=Inorg Chem; citation_author=JJ Engelberts, RWA Havenith, JH Lenthe, LW Jenneskens, PW Fowler; citation_volume=44; citation_publication_date=2005; citation_pages=5266-5272; citation_doi=10.1021/ic050017o; citation_id=CR16
citation_journal_title=Inorg Chem; citation_author=ED Jemmis, B Kiran; citation_volume=37; citation_publication_date=1998; citation_pages=2110-2116; citation_doi=10.1021/ic970737y; citation_id=CR17
citation_journal_title=J Organomet Chem; citation_author=MK Cyrański, TM Krygowski, AR Katritzky, PR Schleyer; citation_volume=67; citation_publication_date=2002; citation_pages=1333-1338; citation_doi=10.1021/jo016255s; citation_id=CR18
citation_journal_title=Tetrahedron; citation_author=MK Cyrański, PR Schleyer, TM Krygowski, H Jiao, G Hohlneicher; citation_volume=59; citation_publication_date=2003; citation_pages=1657-1665; citation_doi=10.1016/S0040-4020(03)00137-6; citation_id=CR19
citation_journal_title=Dalton Trans; citation_author=AK Phukan, AK Guha, B Silvi; citation_volume=39; citation_publication_date=2010; citation_pages=4126-4137; citation_doi=10.1039/b920161k; citation_id=CR20
citation_journal_title=J Phys Chem A; citation_author=W Wu, X Li, L Meng, S Zheng, Y Zeng; citation_volume=119; citation_publication_date=2015; citation_pages=2091-2097; citation_doi=10.1021/jp511862u; citation_id=CR21
citation_journal_title=J Am Chem Soc; citation_author=N Matsunaga, MS Gordon; citation_volume=116; citation_publication_date=1994; citation_pages=11407-11419; citation_doi=10.1021/ja00104a021; citation_id=CR22
citation_journal_title=Comput Theor Chem; citation_author=XJ Feng, M Zhang, LX Zhao, HY Zhang, YH Luo; citation_volume=1029; citation_publication_date=2014; citation_pages=84-90; citation_doi=10.1016/j.comptc.2013.12.015; citation_id=CR23
citation_journal_title=J Phys Chem A; citation_author=PW Fowler, E Steiner; citation_volume=101; citation_publication_date=1997; citation_pages=1409-1413; citation_doi=10.1021/jp9637946; citation_id=CR24
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA et al. (2010) Gaussian 09. Gaussian Inc., Wallingford
citation_journal_title=Phys Rev; citation_author=C Møller, MS Plesset; citation_volume=46; citation_publication_date=1934; citation_pages=618-622; citation_doi=10.1103/PhysRev.46.618; citation_id=CR26
citation_journal_title=J Phys Chem A; citation_author=DE Woon, TH Dunning; citation_volume=103; citation_publication_date=1995; citation_pages=4572-4585; citation_doi=10.1063/1.470645; citation_id=CR27
citation_journal_title=J Phys Chem A; citation_author=TH Dunning; citation_volume=90; citation_publication_date=1989; citation_pages=1007-1023; citation_doi=10.1063/1.456153; citation_id=CR28
citation_journal_title=Mol Phys; citation_author=SF Boys, F Bernardi; citation_volume=19; citation_publication_date=2006; citation_pages=553-566; citation_doi=10.1080/00268977000101561; citation_id=CR29
citation_title=Chemical applications of atomic and molecular electrostatic potentials; citation_publication_date=1981; citation_id=CR30; citation_author=P Politzer; citation_author=DG Truhlar; citation_publisher=Plenum
citation_journal_title=J Mol Model; citation_author=FA Bulat, A Toro-Labbe, T Brinck, JS Murray, P Politzer; citation_volume=16; citation_publication_date=2010; citation_pages=1679-1691; citation_doi=10.1007/s00894-010-0692-x; citation_id=CR31
citation_title=Atoms in molecules—a quantum theory; citation_publication_date=1990; citation_id=CR32; citation_author=RFW Bader; citation_publisher=Oxford University Press
Popelier PLA (2000) Atoms in molecules: an introduction. Pearson, Harlow
citation_title=AIM 2000, version 1.0; citation_publication_date=2000; citation_id=CR34; citation_author=F Biegler-König; citation_publisher=University of Applied Science Bielefeld
citation_journal_title=J Comput Chem; citation_author=T Lu, F Chen; citation_volume=33; citation_publication_date=2012; citation_pages=580-592; citation_doi=10.1002/jcc.22885; citation_id=CR35
citation_journal_title=J Phys Chem A; citation_author=SM Azami; citation_volume=114; citation_publication_date=2010; citation_pages=11794-11797; citation_doi=10.1021/jp1057918; citation_id=CR36
citation_journal_title=ChemPhysChem; citation_author=Y Zeng, M Zhu, L Meng, S Zheng; citation_volume=12; citation_publication_date=2011; citation_pages=3584-3590; citation_doi=10.1002/cphc.201100566; citation_id=CR37
citation_journal_title=ChemPhysChem; citation_author=Y Zeng, W Wu, X Li, S Zheng, L Meng; citation_volume=14; citation_publication_date=2013; citation_pages=1591-1600; citation_doi=10.1002/cphc.201300075; citation_id=CR38
citation_journal_title=C R Acad Sci; citation_author=R Daudel; citation_volume=235; citation_publication_date=1952; citation_pages=886-888; citation_id=CR39
citation_journal_title=J Chim Phys; citation_author=M Roux, S Besnainou, R Daudel; citation_volume=53; citation_publication_date=1956; citation_pages=218-221; citation_doi=10.1051/jcp/1956530218; citation_id=CR40
citation_journal_title=C R Acad Sci; citation_author=M Roux, R Daudel; citation_volume=240; citation_publication_date=1995; citation_pages=90-92; citation_id=CR41
citation_journal_title=Theor Chim Acta; citation_author=SJ Zheng, M Hada, H Nakatsuji; citation_volume=93; citation_publication_date=1996; citation_pages=67-78; citation_doi=10.1007/BF01113548; citation_id=CR42
citation_journal_title=J Mol Model; citation_author=X Li, Y Zeng, X Zhang, S Zheng, L Meng; citation_volume=17; citation_publication_date=2011; citation_pages=757-767; citation_doi=10.1007/s00894-010-0768-7; citation_id=CR43
citation_journal_title=Comput Theor Chem; citation_author=P Politzer, KE Riley, FA Bulat, JS Murray; citation_volume=998; citation_publication_date=2012; citation_pages=2-8; citation_doi=10.1016/j.comptc.2012.06.007; citation_id=CR44