Intrinsic deuterium isotope effects on NMR chemical shifts of hydrogen bonded systems

Hansen, P.

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Tytuł artykułu

Intrinsic deuterium isotope effects on NMR chemical shifts of hydrogen bonded systems

Autorzy

Hansen P.

Treść / Zawartość

Pełne teksty:

Intrinsic deuterium isotope effects on NMR chemical shifts.pdf

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Warianty tytułu

Konferencja

Proceedings of the International Conference “2001 an Isotope Odyssey: New Application for a New Millenium", June 24-29, 2001, Zakopane, Poland

Języki publikacji

Abstrakty

This mini review describes intrinsic deuterium isotope effects on 13C chemical shifts of rigid hydrogen bonded compounds primarily in solution. The steric effects of intramolecularly hydrogen bonded compounds are dissected into different bond interactions leading either to steric compression or to steric twist. One-bond isotope effects involving CH(D) bonds are analyzed in terms of substituent effects and the question is raised whether isotope effects can be useful in the study of CHhydrogen bonds.

Słowa kluczowe

C-H hydrogen bonds deuterium isotope effects intramolecular hydrogen bonds intrinsic isotope effects nuclear shielding steric effects

Wydawca

Institute of Nuclear Chemistry and Technology

Czasopismo

Nukleonika

Rocznik

2002

Tom

Vol. 47,suppl.1

Strony

37--42

Opis fizyczny

Bibliogr. 39 poz., rys.

Twórcy

autor

Hansen P.

Department of Life Sciences and Chemistry, Roskilde University, P.O. Box 260, DK-4000 Roskilde, Denmark, Tel.: +4546742432, Fax: +4546743011, poulerik@ruc.dk

Bibliografia

1. Abildgaard J, Hansen PE (2000) Model quantum-mechanical calculations in chemistry. Wiadomosci Chemiczne 54:846–887 (in Polish)
2. Abildgaard J, Bolvig S, Hansen PE (1998) Unravelling the electronic and vibrational contributions to deuterium isotope effects on 13C chemical shifts using ab initio model calculations. Analysis
of the observed isotope effects on sterically perturbed intramolecular hydrogen-bonded o-hydroxy acyl aromatics. J Am Chem Soc 120:9063–9069
3. Benedict H, Hoelger C, Aguilar-Parilla F, Fehlhammer W-P, Whelan M, Janoscheck R, Limbach H-H (1996) Hydrogen/deuterium isotope effects on the 15N NMR chemical shifts and geometries of low-barrier hydrogen bonds in the solid state. J Mol Struct 378:11–16
4. Benedict H, Limbach H-H, Wehlan M, Fehlhammer W-P, Golubev NS, Janoscheck R (1998) Solid state 15N NMR and theoretical studies of primary and secondary geometric H/D isotope effects on low-barrier NHN-hydrogen bonds. J Am Chem Soc 120:2939–2950
5. Bolvig S, Hansen PE (1996) Deuterium-induced isotope effects on 13C chemical shifts as a probe for tautomerism in enolic β-diketones. Magn Reson Chem 34:467–478
6. Bolvig S, Hansen PE, Wemmer D, Williams P (1999) Deuterium isotope effects on 17O chemical shifts of intramolecularly hydrogen bonded systems. J Mol Struct 509: 171–181
7. Bolvig S, Hansen PE (2000) Isotope effect on chemical shifts, an analytical tool in structural studies of intramolecularly hydrogen bonded compounds. Curr Org Chem 4:19–54
8. Dziembowska T, Rozwadowski Z (2001) Application of the deuterium isotope effect on NMR chemical shift to study proton transfer equilibrium. Curr Org Chem 5:289–313
9. Filarowski A, Koll A, Glowiak T (1999) Steric modification of the intramolecular hydrogen bond in 2-(methylolimino-phenylmethyl)-phenols. Monatsh Chemie 130:1097–1108
10. Forsyth DA, Lucas, P, Burk RM (1982) Conformational dependence of isotope effects for hyperconjugating methyl groups. Nonadditivity of NMR isotope shifts in benzylic ions. J Am Chem Soc 104:240–245
11. Gilli G, Bertulucci F, Ferretti V, Bertolasi V (1989) Evidence for resonance assisted hydrogen bonding from crystal structure correlations on the enol form of the β-diketone fragment. J Am Chem Soc 111:1023–1028
12. Gilli P, Ferretti V, Bertolasi, V, Gilli G (1996) A novel approach to hydrogen bonding theory. Adv Mol Struct Res 2:67–102
13. Gutowsky HS (1959) Isotope effects in high resolution NMR spectroscopy. J Chem Phys 31:1683–1685
14. Hansen PE (1986) Deuterium isotope effects on the 13C nuclear shielding of intramolecularly hydrogen-bonded systems. Org Magn Reson 24:903–910
15. Hansen PE, Nicolaisen FM, Schaumburg K (1986) Deuterium isotope effects on nuclear shielding. Directional effects and nonadditivity in acyl derivatives. J Am Chem Soc 108:625–629
16. Hansen PE, Kawcki R, Krowczynski A, Kozerski L (1990) Deuterium isotope effects on 13C and 15N nuclear shielding in intramolecularly hydrogen-bonded compounds. Investigation of enamine derivatives. Acta Chem Scand 44:826–832
17. Hansen PE (1993) Substituent effects on deuterium isotope effects on nuclear shielding of intramolecularly hydrogen-bonded aromatic ketones, aldehydes and esters. Magn Reson Chem 31:23–37
18. Hansen PE (1993) Long-range deuterium isotope effects on 13C chemical shifts of intramolecularly hydrogen-bonded compounds. Purpurogallins Magn Reson Chem 31:71–74
19. Hansen PE, Hansen Aa E, Lycka A, Buvari-Barcza A (1993) 2∆H(D) and 1∆N(D) isotope effects on nuclear shielding of ammonium ions in complexes with crown ethers and cryptands. Acta Chem Scand 47:777–788
20. Hansen PE, Ibsen SN, Kristensen T, Bolvig S (1994) Deuterium and 18O isotope effects on 13C chemical shifts of sterically hindered and/or intramolecularly hydrogen-bonded o-hydroxy acyl aromatics. Magn Reson Chem 32:399–408
21. Hansen PE, Duus F, Bolvig S, Jagodzinski TS (1996) Intramolecular hydrogen bonding of the enol forms of βketoamides and β-ketoamides. Deuterium isotope effects on 13C chemical shifts. J Mol Struct 378:45–59
22. Hansen PE, Bolvig S, Buvari-Barsza A, Lycka A (1997) Longrange intrinsic and equilibrium deuterium isotope effects on 19F chemical shifts. Acta Chem Scand 51:881–888
23. Hansen PE, Bolvig S (1997) Deuterium isotope effects on 13C chemical shifts of o-hydroxy acylaromatics. Intramolecular hydrogen bonding. Magn Reson Chem 35:520–528
24. Hansen PE, Sitkowski J, Stefaniak L, Rozwadowski Z, Dziembowska, T (1998) One-bond deuterium isotope effects on 15N chemical shifts in Schiff bases. Ber Bunsengesell Phys Chem 102:410–414
25. Hansen PE (2000) Isotope effects on chemical shifts of proteins and peptides. Magn Reson Chem 38:1–10
26. Jameson CJ (1991) The dynamic and electronic factors in isotope effects on NMR parameters. In: Buncel E, Jones JR (eds) Isotopes in physical and biomedical science. Elsevier, Amsterdam
27. LeMaster DM, LaIuppa, JC, Kushlan DM (1994) Differential deuterium isotope shifts and one-bond 1H-13C scalar couplings in the conformational analysis of protein glycine residues. J Biomol NMR 4:863–870
28. Liepins E, Petrova MV, Gudriniece E, Paulins J, Kuznetsov SL (1989) Relationship between 1H, 13C and 17O NMR chemical shifts and H/D isotope effects on 13C and 17O nuclear shieldings in Intrinsic deuterium isotope effects on NMR chemical shifts of hydrogen bonded systems intramolecular hydrogen-bonded systems. Magn Reson Chem 27:907–917
29. Marques MPM, Amorim da Costa AM, Ribeiro-Claro PJA (2001) Evidence of C-H…O hydrogen bonds in liquid 4-ethyoxybenzaldehyde by NMR and vibrational spectroscopies. J Phys Chem A 105:5292–5297
30. Morris DG, Murray AM (1976) Carbon-13 chemical shifts and substituent effects in 4-substituted camphors, N-nitrocamphoimines and diazocamphors. JCS Perkin Trans 2:579–581
31. Munch M, Hansen Aa E, Hansen PE, Bouman TD (1992) Ab initio calculations of deuterium isotope effects on hydrogen and nitrogen nuclear magnetic shielding in the hydrated ammonium ion. Acta Chem Scand 46:1065–1071
32. Rozwadowski Z, Majewski E, Dziembowska T, Hansen PE (1999) Deuterium isotope effects on 13C chemical shifts of intramolecularly hydrogen-bonded Schiff bases. JCS Perkin Trans 2:2809–2817
33. Schah-Mohameddi P, Shenderovich IG, Detering C et al. (2000) Hydrogen/deuterium-isotope effects on NMR chemical shifts and symmetry of homoconjugated hydrogen-bonded ions in polar solutions. J Am Chem Soc 122:12878–12879
34. Smirnow SN, Golubev NS, Denisov GS, Benedict H, SchahMohameddi P, Limbach H-H (1996) Hydrogen/deuterium isotope effects on the NMR chemical shfits and geometries of intermolecular low-barrier hydrogen-bonded complexes. J Am Chem Soc 118:4094–4101
35. Sosnicki JS, Jagodzinski T, Hansen PE, private communication
36. Steiner T (1996) C-H…O hydrogen bonding in crystals. Cryst Rev 6:1–57
37. Tüchsen E, Hansen PE (1991) Hydrogen bonding monitored by deuterium isotope effects on carbonyl 13C chemical shifts in BPTI: intra-residue hydrogen bonds in antiparallel β-sheet. Int J Biomol Macromol 13:1–9
38. Wozniak K, Bolvig S, Hansen PE (2002) Steric compression and twist in o-hydroxy acyl aromatics with intramolecular hydrogen bonding. Phys Chem Chem Phys (submitted)
39. Zheglova DK, Genov DG, Bolvig S, Hansen PE (1997) Deuterium isotope effects on 13C chemical shifts of enaminones. Acta Chem Scand 51:1016–1023

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Bibliografia

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