SCOPUS 정보 검색 플랫폼

Chemistry - A European Journal

Volumn 20, Issue 35, 2014, Pages 11058-11068

Fluorine as a hydrogen-bond acceptor: Experimental evidence and computational calculations

(3) Dalvit, Claudio a Invernizzi, Christian a Vulpetti, Anna b

a UNIVERSITY OF NEUCHÂTEL (Switzerland)

b NOVARTIS PHARMA AG (Switzerland)

Author keywords

fluorine; hydrogen bonds; molecular electrostatic potential; NMR spectroscopy; noncovalent interactions

Indexed keywords

COMPLEXATION; HYDROGEN BONDS; IONS; KETONES; MOLECULAR INTERACTIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CHEMICAL AND BIOLOGICALS; COMPUTATIONAL CALCULATIONS; ELECTRON-DENSITY TOPOLOGY; HYDROGEN BONDING INTERACTIONS; HYDROGEN-BOND COMPLEXES; INTRAMOLECULAR INTERACTIONS; MOLECULAR ELECTROSTATIC POTENTIALS; NON-COVALENT INTERACTION;

FLUORINE;

EID: 84906486351 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201402858 Document Type: Article

Times cited : (155)

References (62)

1
- 49449097238
- W. K. Hagmann, J. Med. Chem. 2008, 51, 4359-4369
- (2008) J. Med. Chem. , vol.51 , pp. 4359-4369
- Hagmann, W.K.¹

2
- 38149070200
- S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320-330
- (2008) Chem. Soc. Rev. , vol.37 , pp. 320-330
- Purser, S.¹ Moore, P.R.² Swallow, S.³ Gouverneur, V.⁴

3
- 33746372978
- K. L. Kirk, J. Fluorine Chem. 2006, 127, 1013-1029
- (2006) J. Fluorine Chem. , vol.127 , pp. 1013-1029
- Kirk, K.L.¹

4
- 4444355871
- H. J. Böhm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Müller, U. Obst-Sander, M. Stahl, ChemBioChem 2004, 5, 637-643
- (2004) ChemBioChem , vol.5 , pp. 637-643
- Böhm, H.J.¹ Banner, D.² Bendels, S.³ Kansy, M.⁴ Kuhn, B.⁵ Müller, K.⁶ Obst-Sander, U.⁷ Stahl, M.⁸

5
- 17644386567
- W. R. Dolbier, J. Fluorine Chem. 2005, 126, 157-163.
- (2005) J. Fluorine Chem. , vol.126 , pp. 157-163
- Dolbier, W.R.¹

6
- 0038413902
- C. D. Murphy, C. Schaffrath, D. O'Hagan, Chemosphere 2003, 52, 455-461.
- (2003) Chemosphere , vol.52 , pp. 455-461
- Murphy, C.D.¹ Schaffrath, C.² O'Hagan, D.³

7
- 34848848499
- K. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881-1886
- (2007) Science , vol.317 , pp. 1881-1886
- Müller, K.¹ Faeh, C.² Diederich, F.³

8
- 84864633171
- A. Vulpetti, C. Dalvit, Drug Discovery Today 2012, 17, 890-897
- (2012) Drug Discovery Today , vol.17 , pp. 890-897
- Vulpetti, A.¹ Dalvit, C.²

9
- 84891494104
- I. NGo, S. Golten, A. Ardá, J. Cañada, J. Jiménez-Barbero, B. Linclau, S. P. Vincent, Chem. Eur. J. 2014, 20, 106-112.
- (2014) Chem. Eur. J. , vol.20 , pp. 106-112
- Ngo, I.¹ Golten, S.² Ardá, A.³ Cañada, J.⁴ Jiménez-Barbero, J.⁵ Linclau, B.⁶ Vincent, S.P.⁷

10
- 38149016915
- D. O'Hagan, Chem. Soc. Rev. 2008, 37, 308-319
- (2008) Chem. Soc. Rev. , vol.37 , pp. 308-319
- O'Hagan, D.¹

11
- 0034926661
- B. E. Smart, J. Fluorine Chem. 2001, 109, 3-11.
- (2001) J. Fluorine Chem. , vol.109 , pp. 3-11
- Smart, B.E.¹

12
- 84855661131
- K. E. Riley, J. S. Murray, J. Fanfrlik, J. Rezac, R. J. Sola, M. C. Concha, F. M. Ramos, P. Politzer, J. Mol. Model. 2011, 17, 3309-3318.
- (2011) J. Mol. Model. , vol.17 , pp. 3309-3318
- Riley, K.E.¹ Murray, J.S.² Fanfrlik, J.³ Rezac, J.⁴ Sola, R.J.⁵ Concha, M.C.⁶ Ramos, F.M.⁷ Politzer, P.⁸

13
- 21244441383
- R. Paulini, K. Müller, F. Diederich, Angew. Chem. 2005, 117, 1820-1839
- (2005) Angew. Chem. , vol.117 , pp. 1820-1839
- Paulini, R.¹ Müller, K.² Diederich, F.³

14
- 17044421336
- Angew. Chem. Int. Ed. 2005, 44, 1788-1805
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 1788-1805

15
- 84893858699
- G. T. Giuffredi, V. Gouverneur, B. Bernet, Angew. Chem. 2013, 125, 10718-10722
- (2013) Angew. Chem. , vol.125 , pp. 10718-10722
- Giuffredi, G.T.¹ Gouverneur, V.² Bernet, B.³

16
- 84884891362
- Angew. Chem. Int. Ed. 2013, 52, 10524-10528
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 10524-10528

17
- 77953104442
- V. K. Batra, L. C. Pedersen, W. A. Beard, S. H. Wilson, B. A. Kashemirov, T. G. Upton, M. F. Goodman, C. E. McKenna, J. Am. Chem. Soc. 2010, 132, 7617-7625.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 7617-7625
- Batra, V.K.¹ Pedersen, L.C.² Beard, W.A.³ Wilson, S.H.⁴ Kashemirov, B.A.⁵ Upton, T.G.⁶ Goodman, M.F.⁷ McKenna, C.E.⁸

18
- 78650552642
- C. Dalvit, A. Vulpetti, ChemMedChem 2011, 6, 104-114
- (2011) ChemMedChem , vol.6 , pp. 104-114
- Dalvit, C.¹ Vulpetti, A.²

19
- 84856382414
- C. Dalvit, A. Vulpetti, ChemMedChem 2012, 7, 262-272.
- (2012) ChemMedChem , vol.7 , pp. 262-272
- Dalvit, C.¹ Vulpetti, A.²

20
- 70350515927
- P. Zhou, J. Zou, F. Tian, Z. Shang, J. Chem. Inf. Model. 2009, 49, 2344-2355.
- (2009) J. Chem. Inf. Model. , vol.49 , pp. 2344-2355
- Zhou, P.¹ Zou, J.² Tian, F.³ Shang, Z.⁴

21
- 0035503446
- C. Ouvrard, M. Berthelot, C. Laurence, J. Phys. Org. Chem. 2001, 14, 804-810
- (2001) J. Phys. Org. Chem. , vol.14 , pp. 804-810
- Ouvrard, C.¹ Berthelot, M.² Laurence, C.³

22
- 0030590426
- J. A. K. Howard, V. J. Hoy, D. O'Hagan, G. T. Smith, Tetrahedron 1996, 52, 12613-12622
- (1996) Tetrahedron , vol.52 , pp. 12613-12622
- Howard, J.A.K.¹ Hoy, V.J.² O'Hagan, D.³ Smith, G.T.⁴

23
- 84868583748
- R. E. Rosenberg, J. Phys. Chem. A 2012, 116, 10842-10849.
- (2012) J. Phys. Chem. A , vol.116 , pp. 10842-10849
- Rosenberg, R.E.¹

24
- 0030937244
- J. D. Dunitz, R. Taylor, Chem. Eur. J. 1997, 3, 89-98.
- (1997) Chem. Eur. J. , vol.3 , pp. 89-98
- Dunitz, J.D.¹ Taylor, R.²

25
- 72949098147
- S. A. Samsonov, M. Salwiczek, G. Anders, B. Koksch, M. T. Pisabarro, J. Phys. Chem. B 2009, 113, 16400-16408.
- (2009) J. Phys. Chem. B , vol.113 , pp. 16400-16408
- Samsonov, S.A.¹ Salwiczek, M.² Anders, G.³ Koksch, B.⁴ Pisabarro, M.T.⁵

26
- 0001108349
- D. Gurka, R. W. Taft, J. Am. Chem. Soc. 1969, 91, 4794-4801
- (1969) J. Am. Chem. Soc. , vol.91 , pp. 4794-4801
- Gurka, D.¹ Taft, R.W.²

27
- 33947301033
- R. W. Taft, D. Gurka, L. Joris, P. von R. Schleyer, J. W. Rakshys, J. Am. Chem. Soc. 1969, 91, 4801-4808
- (1969) J. Am. Chem. Soc. , vol.91 , pp. 4801-4808
- Taft, R.W.¹ Gurka, D.² Joris, L.³ Schleyer, P.V.R.⁴ Rakshys, J.W.⁵

28
- 77953516053
- C. Laurence, J. Graton, M. Berthelot, F. Besseau, J. Y. Le Questel, M. Lucon, C. Ouvrard, A. Planchat, E. Renault, J. Org. Chem. 2010, 75, 4105-4123
- (2010) J. Org. Chem. , vol.75 , pp. 4105-4123
- Laurence, C.¹ Graton, J.² Berthelot, M.³ Besseau, F.⁴ Le Questel, J.Y.⁵ Lucon, M.⁶ Ouvrard, C.⁷ Planchat, A.⁸ Renault, E.⁹

29
- 37049068888
- M. H. Abraham, P. P. Duce, D. V. Prior, D. G. Barratt, J. J. Morris, P. J. Taylor, J. Chem. Soc. Perkin Trans. 2 1989, 1355-1375.
- (1989) J. Chem. Soc. Perkin Trans. 2 , pp. 1355-1375
- Abraham, M.H.¹ Duce, P.P.² Prior, D.V.³ Barratt, D.G.⁴ Morris, J.J.⁵ Taylor, P.J.⁶

30
- 0000758885
- D. Gurka, R. W. Taft, L. Joris, P. V. Schleyer, J. Am. Chem. Soc. 1967, 89, 5957-5958.
- (1967) J. Am. Chem. Soc. , vol.89 , pp. 5957-5958
- Gurka, D.¹ Taft, R.W.² Joris, L.³ Schleyer, P.V.⁴

31
- 0347359145
- C. S. Johnson, Prog. Nucl. Magn. Reson. Spectrosc. 1999, 34, 203-256
- (1999) Prog. Nucl. Magn. Reson. Spectrosc. , vol.34 , pp. 203-256
- Johnson, C.S.¹

32
- 0028327522
- K. F. Morris, P. Stilbs, C. S. Johnson, Anal. Chem. 1994, 66, 211-215
- (1994) Anal. Chem. , vol.66 , pp. 211-215
- Morris, K.F.¹ Stilbs, P.² Johnson, C.S.³

33
- 80054721956
- (Eds.: R. K. Harris, R. E. Wasylishen), Wiley, New York.
- G. A. Morris, in Encyclopedia of Magnetic Resonance (Eds.:, R. K. Harris, R. E. Wasylishen,), Wiley, New York, 2009.
- (2009) Encyclopedia of Magnetic Resonance
- Morris, G.A.¹

34
- 84889880731
- A. Vulpetti, C. Dalvit, ChemMedChem 2013, 8, 2057-2069.
- (2013) ChemMedChem , vol.8 , pp. 2057-2069
- Vulpetti, A.¹ Dalvit, C.²

35
- 70349124638
- A. Vulpetti, U. Hommel, G. Landrum, R. Lewis, C. Dalvit, J. Am. Chem. Soc. 2009, 131, 12949-12959.
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 12949-12959
- Vulpetti, A.¹ Hommel, U.² Landrum, G.³ Lewis, R.⁴ Dalvit, C.⁵

36
- 84893872409
- B. Dugovic, C. J. Leumann, J Org Chem. 2014, 79, 1271-1279
- (2014) J Org Chem. , vol.79 , pp. 1271-1279
- Dugovic, B.¹ Leumann, C.J.²

37
- 84876065455
- N. Martin-Pintado, M. Yahyaee-Anzahaee, G. F. Deleavey, G. Portella, M. Orozco, M. J. Damha, C. Gonzalez, J. Am. Chem. Soc. 2013, 135, 5344-5347
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 5344-5347
- Martin-Pintado, N.¹ Yahyaee-Anzahaee, M.² Deleavey, G.F.³ Portella, G.⁴ Orozco, M.⁵ Damha, M.J.⁶ Gonzalez, C.⁷

38
- 79851485836
- M. Yahyaee Anzahaee, J. K. Watts, N. R. Alla, A. W. Nicholson, M. J. Damha, J. Am. Chem. Soc. 2011, 133, 728-731.
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 728-731
- Yahyaee Anzahaee, M.¹ Watts, J.K.² Alla, N.R.³ Nicholson, A.W.⁴ Damha, M.J.⁵

39
- 84896525124
- A. El Kerdawy, C. S. Tautermann, T. Clark, T. Fox, J. Chem. Inf. Model. 2013, 53, 3262-3272
- (2013) J. Chem. Inf. Model. , vol.53 , pp. 3262-3272
- El Kerdawy, A.¹ Tautermann, C.S.² Clark, T.³ Fox, T.⁴

40
- 84894644436
- A. J. Green, P. L. A. Popelier, J. Chem. Inf. Model. 2014, 54, 553-561.
- (2014) J. Chem. Inf. Model. , vol.54 , pp. 553-561
- Green, A.J.¹ Popelier, P.L.A.²

41
- 84890711200
- Wiley, New York.
- W. R. Dolbier, Jr., Guide to Fluorine NMR for Organic Chemists, Wiley, New York, 2009.
- (2009) Guide to Fluorine NMR for Organic Chemists
- Dolbier, Jr.W.R.¹

42
- 0000346476
- J. S. Murray, S. Ranganathan, P. Politzer, J. Org. Chem. 1991, 56, 3734-3737
- (1991) J. Org. Chem. , vol.56 , pp. 3734-3737
- Murray, J.S.¹ Ranganathan, S.² Politzer, P.³

43
- 66249086550
- P. W. Kenny, J. Chem. Inf. Model. 2009, 49, 1234-1244.
- (2009) J. Chem. Inf. Model. , vol.49 , pp. 1234-1244
- Kenny, P.W.¹

44
- 0345401784
- R. F. W. Bader, Chem. Rev. 1991, 91, 893-928
- (1991) Chem. Rev. , vol.91 , pp. 893-928
- Bader, R.F.W.¹

45
- 77952032315
- E. R. Johnson, S. Keinan, P. Mori-Sanchez, J. Contreras-Garcia, A. J. Cohen, W. T. Yang, J. Am. Chem. Soc. 2010, 132, 6498-6506.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 6498-6506
- Johnson, E.R.¹ Keinan, S.² Mori-Sanchez, P.³ Contreras-Garcia, J.⁴ Cohen, A.J.⁵ Yang, W.T.⁶

46
- 33645506083
- R. Parthasarathi, V. Subramanian, N. Sathyamurthy, J. Phys. Chem. A 2006, 110, 3349-3351.
- (2006) J. Phys. Chem. A , vol.110 , pp. 3349-3351
- Parthasarathi, R.¹ Subramanian, V.² Sathyamurthy, N.³

47
- 0000985307
- R. W. Taft, I. C. Lewis, G. T. Davis, I. R. Fox, K. K. Andersen, E. Price, J. Am. Chem. Soc. 1963, 85, 3146-3156.
- (1963) J. Am. Chem. Soc. , vol.85 , pp. 3146-3156
- Taft, R.W.¹ Lewis, I.C.² Davis, G.T.³ Fox, I.R.⁴ Andersen, K.K.⁵ Price, E.⁶

48
- 0038207989
- C. Dalvit, P. E. Fagerness, D. T. Hadden, R. W. Sarver, B. J. Stockman, J. Am. Chem. Soc. 2003, 125, 7696-7703
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 7696-7703
- Dalvit, C.¹ Fagerness, P.E.² Hadden, D.T.³ Sarver, R.W.⁴ Stockman, B.J.⁵

49
- 84863052839
- J. B. Jordan, L. Poppe, X. Y. Xia, A. C. Cheng, Y. Sun, K. Michelsen, H. Eastwood, P. D. Schnier, T. Nixey, W. G. Zhong, J. Med. Chem. 2012, 55, 678-687
- (2012) J. Med. Chem. , vol.55 , pp. 678-687
- Jordan, J.B.¹ Poppe, L.² Xia, X.Y.³ Cheng, A.C.⁴ Sun, Y.⁵ Michelsen, K.⁶ Eastwood, H.⁷ Schnier, P.D.⁸ Nixey, T.⁹ Zhong, W.G.¹⁰

50
- 1642296510
- T. Tengel, T. Fex, H. Emtenas, F. Almqvist, I. Sethson, J. Kihlberg, Org. Biomol. Chem. 2004, 2, 725-731
- (2004) Org. Biomol. Chem. , vol.2 , pp. 725-731
- Tengel, T.¹ Fex, T.² Emtenas, H.³ Almqvist, F.⁴ Sethson, I.⁵ Kihlberg, J.⁶

51
- 84859172058
- M. Braitsch, H. Kählig, G. Kontaxis, M. Fischer, T. Kawada, R. Konrat, W. Schmid, Beilstein J. Org. Chem. 2012, 8, 448-455.
- (2012) Beilstein J. Org. Chem. , vol.8 , pp. 448-455
- Braitsch, M.¹ Kählig, H.² Kontaxis, G.³ Fischer, M.⁴ Kawada, T.⁵ Konrat, R.⁶ Schmid, W.⁷

52
- 36049036606
- C. Dalvit, Prog. Nucl. Magn. Reson. Spectrosc. 2007, 51, 243-271.
- (2007) Prog. Nucl. Magn. Reson. Spectrosc. , vol.51 , pp. 243-271
- Dalvit, C.¹

53
- 78349294513
- A. Vulpetti, N. Schiering, C. Dalvit, Proteins Struct. Funct. Bioinf. 2010, 78, 3281-3291.
- (2010) Proteins Struct. Funct. Bioinf. , vol.78 , pp. 3281-3291
- Vulpetti, A.¹ Schiering, N.² Dalvit, C.³

54
- 84867807912
- Y. Lee, H. Zeng, S. Ruedisser, A. D. Gossert, C. Hilty, J. Am. Chem. Soc. 2012, 134, 17448-17451.
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 17448-17451
- Lee, Y.¹ Zeng, H.² Ruedisser, S.³ Gossert, A.D.⁴ Hilty, C.⁵

55
- 53849096731
- P. A. Sigala, D. A. Kraut, J. M. M. Caaveiro, B. Pybus, E. A. Ruben, D. Ringe, G. A. Petsko, D. Herschlag, J. Am. Chem. Soc. 2008, 130, 13696-13708.
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 13696-13708
- Sigala, P.A.¹ Kraut, D.A.² Caaveiro, J.M.M.³ Pybus, B.⁴ Ruben, E.A.⁵ Ringe, D.⁶ Petsko, G.A.⁷ Herschlag, D.⁸

56
- 0023893819
- L. B. Dugad, J. T. Gerig, Biochemistry 1988, 27, 4310-4316
- (1988) Biochemistry , vol.27 , pp. 4310-4316
- Dugad, L.B.¹ Gerig, J.T.²

57
- 33846320455
- V. M. Krishnamurthy, B. R. Bohall, C. Y. Kim, D. T. Moustakas, D. W. Christianson, G. M. Whitesides, Chem. Asian J. 2007, 2, 94-105.
- (2007) Chem. Asian J. , vol.2 , pp. 94-105
- Krishnamurthy, V.M.¹ Bohall, B.R.² Kim, C.Y.³ Moustakas, D.T.⁴ Christianson, D.W.⁵ Whitesides, G.M.⁶

58
- 36849135646
- T. J. Swift, R. E. Connick, J. Chem. Phys. 1962, 37, 307-320.
- (1962) J. Chem. Phys. , vol.37 , pp. 307-320
- Swift, T.J.¹ Connick, R.E.²

59
- 0032509252
- D. Albanese, D. Landini, M. Penso, J. Org. Chem. 1998, 63, 9587-9589.
- (1998) J. Org. Chem. , vol.63 , pp. 9587-9589
- Albanese, D.¹ Landini, D.² Penso, M.³

60
- 0000886363
- J. M. Böhlen, M. Rey, G. Bodenhausen, J. Magn. Reson. 1989, 84, 191-197
- (1989) J. Magn. Reson. , vol.84 , pp. 191-197
- Böhlen, J.M.¹ Rey, M.² Bodenhausen, G.³

61
- 0030631673
- T.-L. Hwang, P. C. M. van Zijl, M. Garwood, J. Magn. Reson. 1997, 124, 250-254.
- (1997) J. Magn. Reson. , vol.124 , pp. 250-254
- Hwang, T.-L.¹ Van Zijl, P.C.M.² Garwood, M.³

62
- 30444437574
- G. A. Kaminski, J. R. Maple, R. B. Murphy, D. A. Braden, R. A. Friesner, J. Chem. Theory Comput. 2005, 1, 248-254.
- (2005) J. Chem. Theory Comput. , vol.1 , pp. 248-254
- Kaminski, G.A.¹ Maple, J.R.² Murphy, R.B.³ Braden, D.A.⁴ Friesner, R.A.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.