Hydrogen bonds and ionic interactions in Guanidine/Guanidinium complexes: A computational case study

Structural Chemistry

Volumn 19, Issue 6, 2008, Pages 923-933

  Rozas, Isabel ^a   Alkorta, Ibon ^b   Elguero, José ^b  

^a TRINITY COLLEGE DUBLIN   (Ireland)

^b INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

Ab initio; AIM; DFT; Guanidinium; Hydrogen bonds; Ionic interaction; NBO

Indexed keywords

EID: 56549090676     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11224-008-9377-9     Document Type: Article

References (61)

1. P Gilli V Bertolasi V Ferretti G Gilli 1994 J Am Chem Soc 116 909 10.1021/ja00082a011
2. P Gilli V Bertolasi L Pretto V Ferretti G Gilli 2004 J Am Chem Soc 126 3845 10.1021/ja030213z
3. G Gilli P Gilli 2000 J Mol Struct 552 1 10.1016/S0022-2860(00)00454-3
4. P Gilli V Bertolasi V Ferretti G Gilli 2000 J Am Chem Soc 122 10405 10.1021/ja000921+
5. P Gilli V Bertolasi L Pretto A Lyčka G Gilli 2002 J Am Chem Soc 124 13554 10.1021/ja020589x
6. D Braga K Rubini L Maini 2004 Cryst Eng Comm 6 236 10.1039/b409904b
7. V Ferretti V Bertolasi L Pretto 2004 N J Chem 26 646 10.1039/b314143h
8. Mascal M, Marjo CE, Blake AJ (2000) Chem Commun (Camb) 1591. doi: 10.1039/b002361m
9. D Braga L Maini F Grepioni A De Cian O Felix J Fischer 2000 N J Chem 24 547 10.1039/b002061n
10. Braga D, Angelino A, Tagliavini E, Grepioni F (1998) J Chem Soc Dalton Trans 1961. doi: 10.1039/a800914g
11. D Braga F Grepioni 1997 Acc Chem Res 30 81 10.1021/ar9602009
12. Tsoucaris G (ed) (1998) Current challenges on large supramolecular assemblies. Kluwer, Dordrecht
13. L Brammer JK Swearingen EA Bruton P Sherwood 2002 Proc Natl Acad Sci USA 99 4956 10.1073/pnas.072623399
14. SO Lee DM Shacklady MJ Horner S Ferlay MW Hosseini MD Ward 2005 Cryst Growth Des 5 995 10.1021/cg049660w
15. SU Son JA Reingold GB Carpenter PT Czech DA Sweigart 2006 Organometallics 25 5276 10.1021/om0604425
16. AH Pakiari K Eskandari 2006 J Mol Struct Theochem 759 51 10.1016/j.theochem.2005.10.040
17. Recommendation from IUPAC Task Group 2004-026-2-100. May 2007. E. Arunan personal communication
18. M Meot-Ner 2005 Chem Rev 105 213 10.1021/cr9411785
19. I Mayer I Lukovits T Radnai 1992 Chem Phys Lett 188 595 10.1016/0009-2614(92)80872-9
20. JB Levy 1998 Struct Chem 9 179 10.1023/A:1022466913479
21. P Ayotte SB Nielsen GH Weddle MA Johnson SS Xantheas 1999 J Phys Chem A 103 10665 10.1021/jp991963r
22. Garrett BC, Dixon DA, Camaioni DM, Chipman DM, Johnson MA, Jonah CD, Kimmel GA, Miller JH, Rescigno TN, Rossky PJ, Xantheas SS, Colson SD, Laufer AH, Ray D, Barbara PF, Bartels DM, Becker KH, Bowen H, Bradforth SE, Carmichael I, Coe JV, Corrales LR, Cowin JP, Dupuis M, Eisenthal KB, Franz JA, Gutowski MS, Jordan KD, Kay BD, LaVerne JA, Lymar SV, Madey TE, McCurdy CW, Meisel D, Mukamel S, Nilsson AR, Orlando TM, Petrik NG, Pimblott SM, Rustad JR, Schenter GK, Singer SJ, Tokmakoff A, Wang LS, Wittig C, Zwier TS (2005) Chem Rev 105:355. doi: 10.1021/cr030453x
23. Y Chen T Kortemme T Robertson D Baker G Varani 2004 Nucleic Acids Res 32 5147 10.1093/nar/gkh785
24. O Félix MW Hosseini A De Cian J Fischer 1997 Angew Chem Int Ed Engl 36 102 10.1002/anie.199701021
25. S Kim HF Schaefer III 2007 J Phys Chem A 111 10381 10.1021/jp072727g
26. S Kim HF Schaefer III 2007 J Chem Phys 125 144305 10.1063/1.2356464
27. P Botschwina R Oswald V Dyczmons 2007 Int J Mass Spectrom 267 308 10.1016/j.ijms.2007.02.057
28. VA Russell MC Etter MD Ward 1994 Chem Mater 6 1206 10.1021/cm00044a019
29. I Rozas PE Kruger 2005 J Chem Theory Comput 1 1055 10.1021/ct050009x
30. Bader RFW (1990) Atoms in molecules. A quantum theory. Oxford University, New York
31. FW Bieger-Konig RFW Bader TH Tang 1982 J Comput Chem 3 317 10.1002/jcc.540030306
32. AE Reed LA Curtiss F Weinhold 1988 Chem Rev 88 899 10.1021/cr00088a005
33. Weinhold F, Carpenter JE (1988) In: Naaman R, Vager Z (eds) The structure of small molecules, NBO version 3.1, Plenum, New York
34. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, revision C.02. Gaussian, Inc., Wallingford, CT
35. PC Hariharan JA Pople 1973 Theor Chim Acta 28 213 10.1007/BF00533485
36. PC Hariharan JA Pople 1974 Mol Phys 27 209 10.1080/00268977400100171
37. A Schaefer C Huber R Ahlrichs 1994 J Chem Phys 100 5829 10.1063/1.467146
38. M Head-Gordon JA Pople MJ Frisch 1988 Chem Phys Lett 153 503 10.1016/0009-2614(88)85250-3
39. MJ Frisch M Head-Gordon JA Pople 1990 Chem Phys Lett 166 275 10.1016/0009-2614(90)80029-D
40. MJ Frisch M Head-Gordon JA Pople 1990 Chem Phys Lett 166 281 10.1016/0009-2614(90)80030-H
41. R Krishnan JS Binkley R Seeger JA Pople 1980 J Chem Phys 72 650 10.1063/1.438955
42. DE Woon TH Dunning Jr 1993 J Chem Phys 98 1358 10.1063/1.464303
43. TH Dunning Jr 1989 J Chem Phys 90 1007 10.1063/1.456153
44. JA Montgomery Jr MJ Frisch JW Ochterski GA Petersson 2000 J Chem Phys 112 6532 10.1063/1.481224
45. LA Curtiss PC Redfern K Raghavachari V Rassolov JA Pople 1999 J Chem Phys 110 4703 10.1063/1.478385
46. SB Boys F Bernardi 1970 Mol Phys 19 553 10.1080/00268977000101561
47. I Alkorta O Picazo 2005 Arkivoc ix 305
48. JT Koskinen 1998 Z Naturforsch B Chem Sci 53 386
49. Aue DH, Bowers MT (1979) In: Bowers MT (ed) Gas phase chemistry, vol 2, chap 9. Academic Press, New York
50. A Bondi 1964 J Phys Chem 68 441 10.1021/j100785a001
51. I Alkorta I Rozas J Elguero 1998 Chem Soc Rev 27 163 10.1039/a827163z
52. I Rozas I Alkorta J Elguero 2000 J Am Chem Soc 122 11154 10.1021/ja0017864
53. I Alkorta I Rozas J Elguero 1998 Struct Chem 9 243 10.1023/A: 1022424228462
54. I Alkorta L Barrios I Rozas J Elguero 2000 J Mol Struct Theochem 496 131 10.1016/S0166-1280(99)00177-3
55. E Espinosa I Alkorta J Elguero E Molins 2002 J Chem Phys 117 5529 10.1063/1.1501133
56. I Rozas I Alkorta J Elguero 1998 J Phys Chem A 48 102
57. KB Wiberg PR Rablen 1993 J Comput Chem 14 1504 10.1002/jcc.540141213
58. Weinhold F, Landis CR (2005) Valency and bonding. A natural bond orbital donor-aceptor perspective. Cambridge Press, Cambridge, p 611
59. I Rozas I Alkorta J Elguero 2004 J Phys Chem B 108 3335 10.1021/jp036901m
60. I Rozas I Alkorta J Elguero 2005 Org Biomol Chem 3 366 10.1039/b415768k
61. McNaught AD, Wilkinson A (1997) IUPAC compendium of chemical terminology, 2nd edn. IUPAC, NY