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Volumn 19, Issue 1, 2014, Pages 1069-1084

Concerted halogen bonding and orthogonal metal-halogen interactions in dimers of lithium formamidinate and halogenated formamidines: An ab initio study

Author keywords

Ab initio; Halogen bonding; Orthogonal self Assembling interactions; QTAIM

Indexed keywords

BROMINATED HYDROCARBON; CHLORINATED HYDROCARBON; COORDINATION COMPOUND; FORMAMIDE DERIVATIVE; IODINATED HYDROCARBON; LITHIUM;

EID: 84893085855     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19011069     Document Type: Article
Times cited : (13)

References (51)
  • 1
    • 0035907730 scopus 로고    scopus 로고
    • Halogen bonding: A paradigm in supramolecular chemistry
    • Metrangolo, P.; Resnati, G. Halogen bonding: A paradigm in supramolecular chemistry. Chem. Eur. J. 2001, 7, 2511-2519.
    • (2001) Chem. Eur. J. , vol.7 , pp. 2511-2519
    • Metrangolo, P.1    Resnati, G.2
  • 2
    • 20444479110 scopus 로고    scopus 로고
    • Halogen bonding based recognition processes: A world parallel to hydrogen bonding
    • Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Halogen bonding based recognition processes: A world parallel to hydrogen bonding. Acc. Chem. Res. 2005, 38, 386-395.
    • (2005) Acc. Chem. Res. , vol.38 , pp. 386-395
    • Metrangolo, P.1    Neukirch, H.2    Pilati, T.3    Resnati, G.4
  • 3
    • 77954593406 scopus 로고    scopus 로고
    • Halogen bonding: An electrostatically driven highly directional noncovalent interaction
    • Politzer, P.; Murray, J.S.; Clark, T. Halogen bonding: An electrostatically driven highly directional noncovalent interaction. Phys. Chem. Chem. Phys. 2010, 12, 7748-7757.
    • (2010) Phys. Chem. Chem. Phys. , vol.12 , pp. 7748-7757
    • Politzer, P.1    Murray, J.S.2    Clark, T.3
  • 4
    • 77954598483 scopus 로고    scopus 로고
    • The halogen bond: An interim perspective
    • Legon, A.C. The halogen bond: An interim perspective. Phys. Chem. Chem. Phys. 2010, 12, 7736-7747.
    • (2010) Phys. Chem. Chem. Phys. , vol.12 , pp. 7736-7747
    • Legon, A.C.1
  • 8
    • 84877734097 scopus 로고    scopus 로고
    • Halogen bonding and other s-hole interactions: A perspective
    • Politzer, P.; Murray, J.S.; Clark, T. Halogen bonding and other s-hole interactions: A perspective. Phys. Chem. Chem. Phys. 2013, 15, 11178-11189.
    • (2013) Phys. Chem. Chem. Phys. , vol.15 , pp. 11178-11189
    • Politzer, P.1    Murray, J.S.2    Clark, T.3
  • 9
    • 77953293767 scopus 로고    scopus 로고
    • Halogen bonding: A lump-hole interaction
    • Eskandari, K.; Zariny, H. Halogen bonding: A lump-hole interaction. Chem. Phys. Lett. 2010, 492, 9-13.
    • (2010) Chem. Phys. Lett. , vol.492 , pp. 9-13
    • Eskandari, K.1    Zariny, H.2
  • 10
    • 84875979464 scopus 로고    scopus 로고
    • Halogen bonds: Benchmarks and theoretical analysis
    • Kozuch, S.; Martin, J.M.L. Halogen bonds: Benchmarks and theoretical analysis. J. Chem. Theory Comput. 2013, 9, 1918-1931.
    • (2013) J. Chem. Theory Comput. , vol.9 , pp. 1918-1931
    • Kozuch, S.1    Martin, J.M.L.2
  • 11
    • 84887847433 scopus 로고    scopus 로고
    • On the reliability of pure and hybrid DFT methods for the evaluation of halogen, chalcogen, and pnicogen bonds involving anionic and neutral electron donors
    • Bauzá, A.; Alkorta, I.; Frontera, A.; Elguero, J. On the reliability of pure and hybrid DFT methods for the evaluation of halogen, chalcogen, and pnicogen bonds involving anionic and neutral electron donors. J. Chem. Theory Comput. 2013, 9, 5201-5210.
    • (2013) J. Chem. Theory Comput. , vol.9 , pp. 5201-5210
    • Bauzá, A.1    Alkorta, I.2    Frontera, A.3    Elguero, J.4
  • 13
    • 84859761485 scopus 로고    scopus 로고
    • Halogen bonding in solution
    • Erdelyi, M. Halogen bonding in solution. Chem. Soc. Rev. 2012, 41, 3547-3557.
    • (2012) Chem. Soc. Rev. , vol.41 , pp. 3547-3557
    • Erdelyi, M.1
  • 14
  • 15
    • 84888619396 scopus 로고    scopus 로고
    • The halogen bond in the design of functional supramolecular materials: Recent advances
    • Priimagi, A.; Cavallo, G.; Metrangolo, P.; Resnati, G. The halogen bond in the design of functional supramolecular materials: Recent advances. Acc. Chem. Res. 2013, 46, 2686-2695.
    • (2013) Acc. Chem. Res. , vol.46 , pp. 2686-2695
    • Priimagi, A.1    Cavallo, G.2    Metrangolo, P.3    Resnati, G.4
  • 18
    • 84874632186 scopus 로고    scopus 로고
    • Principles and applications of halogen bonding in medicinal chemistry and chemical biology
    • Wilcken, R.; Zimmernmann, M.O.; Lange A.; Joerger, A.C.; Boeckler, F.M. Principles and applications of halogen bonding in medicinal chemistry and chemical biology. J. Med. Chem. 2013, 56, 1363-1388.
    • (2013) J. Med. Chem. , vol.56 , pp. 1363-1388
    • Wilcken, R.1    Zimmernmann, M.O.2    Lange, A.3    Joerger, A.C.4    Boeckler, F.M.5
  • 19
    • 84872057647 scopus 로고    scopus 로고
    • Plugging the explicit s-holes in molecular docking
    • Kolar, M.; Hobza, P.; Bronowska, A.K. Plugging the explicit s-holes in molecular docking. Chem. Commun. 2013, 49, 981-983.
    • (2013) Chem. Commun. , vol.49 , pp. 981-983
    • Kolar, M.1    Hobza, P.2    Bronowska, A.K.3
  • 20
    • 35348945340 scopus 로고    scopus 로고
    • S-Hole bonding and hydrogen bonding: Competitive interactions
    • Politzer, P.; Murray, J.S.; Lane, P. s-Hole bonding and hydrogen bonding: Competitive interactions. Int. J. Quantum Chem. 2007, 107, 3046-3052.
    • (2007) Int. J. Quantum Chem. , vol.107 , pp. 3046-3052
    • Politzer, P.1    Murray, J.S.2    Lane, P.3
  • 21
    • 84878050391 scopus 로고    scopus 로고
    • Halogen bonding versus hydrogen bonding: What does the Cambridge Database reveal?
    • Mooibroek, T.J.; Gamez, P. Halogen bonding versus hydrogen bonding: What does the Cambridge Database reveal? CrystEngComm. 2013, 15, 4565-4570.
    • (2013) CrystEngComm. , vol.15 , pp. 4565-4570
    • Mooibroek, T.J.1    Gamez, P.2
  • 23
    • 1642538258 scopus 로고    scopus 로고
    • Halogen bonding and hydrogen bonding coexist in driving self-Assembly process
    • Zhu, S.; Xing, C.; Xu, W.; Jin, G.; Li, Z. Halogen bonding and hydrogen bonding coexist in driving self-Assembly process. Cryst. Growth Des. 2004, 4, 53-56.
    • (2004) Cryst. Growth Des. , vol.4 , pp. 53-56
    • Zhu, S.1    Xing, C.2    Xu, W.3    Jin, G.4    Li, Z.5
  • 24
    • 49649098999 scopus 로고    scopus 로고
    • Halogens versus hydrogen
    • Metrangolo, P.; Resnati, G. Halogens versus hydrogen. Science 2008, 321, 918-919.
    • (2008) Science , vol.321 , pp. 918-919
    • Metrangolo, P.1    Resnati, G.2
  • 25
    • 84856907500 scopus 로고    scopus 로고
    • Characteristics and nature of halogen bonds in linear clusters of NCX (X=Cl, and Br): An ab initio, NBO, and QTAIM study
    • Esrafili, M.D.; Hadipour, N.L. Characteristics and nature of halogen bonds in linear clusters of NCX (X=Cl, and Br): An ab initio, NBO, and QTAIM study. Mol. Phys. 2011, 109, 2451-2460.
    • (2011) Mol. Phys. , vol.109 , pp. 2451-2460
    • Esrafili, M.D.1    Hadipour, N.L.2
  • 26
    • 60349086808 scopus 로고    scopus 로고
    • A computational study of the cooperativity in clusters of interhalogen derivatives
    • Alkorta, I.; Blanco, F.; Elguero, J. A computational study of the cooperativity in clusters of interhalogen derivatives. Struct. Chem. 2009, 20, 63-71.
    • (2009) Struct. Chem. , vol.20 , pp. 63-71
    • Alkorta, I.1    Blanco, F.2    Elguero, J.3
  • 27
    • 33746353427 scopus 로고    scopus 로고
    • Cooperativity halogen bonding effect-Ab initio calculations on H2CO?(ClF)n complexes
    • Grabowski, S.J.; Bilewicz, E. Cooperativity halogen bonding effect-Ab initio calculations on H2CO?(ClF)n complexes. Chem. Phys. Lett. 2006, 427, 51-55.
    • (2006) Chem. Phys. Lett. , vol.427 , pp. 51-55
    • Grabowski, S.J.1    Bilewicz, E.2
  • 32
    • 84867139904 scopus 로고    scopus 로고
    • Dimers and trimers of formamidine and its mono-halogenated analogues HNCHNHX, (X = H, Cl, Br, or I): A comparative study of resonance-Assisted hydrogen and halogen bonds
    • Parra, R.D. Dimers and trimers of formamidine and its mono-halogenated analogues HNCHNHX, (X = H, Cl, Br, or I): A comparative study of resonance-Assisted hydrogen and halogen bonds. Comp. Theor. Chem. 2012, 998, 183-192.
    • (2012) Comp. Theor. Chem. , vol.998 , pp. 183-192
    • Parra, R.D.1
  • 34
    • 67849128457 scopus 로고    scopus 로고
    • Halogen bonds as orthogonal molecular interactions to hydrogen bonds
    • Voth, A.R.; Khuu, P.; Oishi, K.; Ho, P.S. Halogen bonds as orthogonal molecular interactions to hydrogen bonds. Nat. Chem. 2009, 1, 74-79.
    • (2009) Nat. Chem. , vol.1 , pp. 74-79
    • Voth, A.R.1    Khuu, P.2    Oishi, K.3    Ho, P.S.4
  • 35
    • 77954743940 scopus 로고    scopus 로고
    • Unexpected "amphoteric" character of the halogen bond: The charge density study of the co-crystal of N-methylpyrazine iodide with I2
    • Nelyubina, Y.V.; Antipin, M.Y.; Dunin, D.S.; Kotov, V.Y.; Lyssenko, K.A. Unexpected "amphoteric" character of the halogen bond: The charge density study of the co-crystal of N-methylpyrazine iodide with I2. Chem. Commun. 2010, 46, 5325-5327.
    • (2010) Chem. Commun. , vol.46 , pp. 5325-5327
    • Nelyubina, Y.V.1    Antipin, M.Y.2    Dunin, D.S.3    Kotov, V.Y.4    Lyssenko, K.A.5
  • 36
    • 79953893336 scopus 로고    scopus 로고
    • Halogen as halogen-bonding donor and hydrogen-bonding acceptor simultaneously in ring-shaped H3N.X(Y).HF (X = Cl, Br and Y = F, Cl, Br) Complexes
    • Zhou, P.-P.; Qiu, W.-Y.; Liu, S.; Jinc, N.-Z. Halogen as halogen-bonding donor and hydrogen-bonding acceptor simultaneously in ring-shaped H3N.X(Y).HF (X = Cl, Br and Y = F, Cl, Br) Complexes. Phys. Chem. Chem. Phys. 2011, 13, 7408-7418.
    • (2011) Phys. Chem. Chem. Phys. , vol.13 , pp. 7408-7418
    • Zhou, P.-P.1    Qiu, W.-Y.2    Liu, S.3    Jinc, N.-Z.4
  • 37
    • 84859409638 scopus 로고    scopus 로고
    • Evidence for the "Amphoteric"nature of fluorine in halogen bonds: An instance of Cl•••F contact
    • Dikundwar, A.G.; Row, T.N.G. Evidence for the "Amphoteric" nature of fluorine in halogen bonds: An instance of Cl•••F contact. Cryst. Growth Des. 2012, 12, 1713-1716.
    • (2012) Cryst. Growth Des. , vol.12 , pp. 1713-1716
    • Dikundwar, A.G.1    Row, T.N.G.2
  • 39
    • 0034300441 scopus 로고    scopus 로고
    • A road map for the calculation of molecular binding energies
    • Dunning, T.H. A road map for the calculation of molecular binding energies. J. Phys. Chem. A 2000, 104, 9062-9080.
    • (2000) J. Phys. Chem. A , vol.104 , pp. 9062-9080
    • Dunning, T.H.1
  • 40
    • 33746614482 scopus 로고
    • Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen
    • Dunning, T.H. Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen. J. Phys. Chem. A 1989, 90, 1007-1023.
    • (1989) J. Phys. Chem. A , vol.90 , pp. 1007-1023
    • Dunning, T.H.1
  • 41
    • 34047140309 scopus 로고    scopus 로고
    • Energy-consistent relativistic pseudopotentials and correlation consistent basis sets for the 4d elements Y-Pd
    • Peterson, K.A.; Figgen, D.; Dolg, M.; Stoll, H. Energy-consistent relativistic pseudopotentials and correlation consistent basis sets for the 4d elements Y-Pd. J. Chem. Phys. 2007, 126, 124101.
    • (2007) J. Chem. Phys. , vol.126 , pp. 124101
    • Peterson, K.A.1    Figgen, D.2    Dolg, M.3    Stoll, H.4
  • 42
    • 84890021933 scopus 로고
    • Calculation of small molecular interactions by differences of separate total energies-some procedures with reduced errors
    • Boys, S.F.; Bernardi, F. Calculation of small molecular interactions by differences of separate total energies -some procedures with reduced errors. Mol. Phys. 1970, 19, 553-566.
    • (1970) Mol. Phys. , vol.19 , pp. 553-566
    • Boys, S.F.1    Bernardi, F.2
  • 44
    • 0035871851 scopus 로고    scopus 로고
    • AIM2000-A program to analyze and visualize atoms in molecules
    • Biegler-König, F.; Schönbohm, J.; Bayles, D. AIM2000 -A program to analyze and visualize atoms in molecules. J. Comput. Chem. 2001, 22, 545-559.
    • (2001) J. Comput. Chem. , vol.22 , pp. 545-559
    • Biegler-König, F.1    Schönbohm, J.2    Bayles, D.3
  • 45
    • 84892713714 scopus 로고    scopus 로고
    • TK Gristmill Software; Overland Park, KS, USA
    • Keith, T.A. AIMAll (Version 13.11.04), TK Gristmill Software; Overland Park, KS, USA, 2013.
    • (2013) AIMAll (Version 13.11.04)
    • Keith, T.A.1
  • 46
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. III. The role of exact exchange
    • Becke, A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98, 5648-5652.
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 47
    • 84857416698 scopus 로고    scopus 로고
    • QTAIM characteristics of halogen bond and related interactions
    • Grabowski, S.J. QTAIM Characteristics of halogen bond and related interactions. J. Phys. Chem. A 2012, 116, 1838-1845.
    • (2012) J. Phys. Chem. A , vol.116 , pp. 1838-1845
    • Grabowski, S.J.1
  • 48
    • 79954529867 scopus 로고    scopus 로고
    • What is the covalency of hydrogen bonding?
    • Grabowski, S.J. What is the covalency of hydrogen bonding? Chem. Rev. 2011, 111, 2597-2625.
    • (2011) Chem. Rev. , vol.111 , pp. 2597-2625
    • Grabowski, S.J.1
  • 49
    • 35748963867 scopus 로고    scopus 로고
    • Ab initio investigation of the complexes between bromobenzene and several electron donors: Some insights into the magnitude and nature of halogen bonding interactions
    • Lu, Y.-X.; Zou, J.-W.; Wang, Y.-H.; Jiang, Y.-J.; Yu, Q.-S. Ab initio investigation of the complexes between bromobenzene and several electron donors: Some insights into the magnitude and nature of halogen bonding interactions. J. Phys. Chem. A 2007, 111, 10781-10788.
    • (2007) J. Phys. Chem. A , vol.111 , pp. 10781-10788
    • Lu, Y.-X.1    Zou, J.-W.2    Wang, Y.-H.3    Jiang, Y.-J.4    Yu, Q.-S.5
  • 50
    • 84868021265 scopus 로고    scopus 로고
    • Advanced supramolecular polymers constructed by orthogonal self-Assembly
    • Li, S.-L.; Xiao, T.; Lin, C.; Wang, L. Advanced supramolecular polymers constructed by orthogonal self-Assembly. Chem. Soc. Rev. 2012, 41, 5950-5968.
    • (2012) Chem. Soc. Rev. , vol.41 , pp. 5950-5968
    • Li, S.-L.1    Xiao, T.2    Lin, C.3    Wang, L.4
  • 51
    • 84897584703 scopus 로고    scopus 로고
    • Functional systems with orthogonal dynamic covalent bonds
    • advanced article. doi:10.1039/C3CS60342C
    • Wilson, A.; Gasparini, G.; Matile, S. Functional systems with orthogonal dynamic covalent bonds. Chem. Soc. Rev. 2014, advanced article. doi:10.1039/C3CS60342C.
    • (2014) Chem. Soc. Rev.
    • Wilson, A.1    Gasparini, G.2    Matile, S.3


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