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Structure, Electronic Properties and NMR-Shielding of Cucurbit[n]urils

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Abstract

Geometries, electronic properties and NMR-shielding of cucurbit[5]uril, decamethylcucurbit[5]uril, cucurbit[6]uril, cucurbit[7]uril, and cucurbit[8]uril are investigated with DFT calculations. All molecules are highly symmetrical with a distinct geometric flexibility. In addition with a characteristic partial charge distribution these findings account for their chemical complex building ability.

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References

  1. R. Behrend E. Meyer F. Rusche (1905) Ann. Chem 339 1

    Google Scholar 

  2. W.A. Freeman W.L. Mock N.-Y. Shih (1981) J. Am. Chem. Soc. 103 7367 Occurrence Handle1:CAS:528:DyaL38XmvV2mtA%3D%3D

    CAS  Google Scholar 

  3. W.A Freeman (1984) Acta Cryst. B40 382 Occurrence Handle1:CAS:528:DyaL2cXlt1Srsb4%3D

    CAS  Google Scholar 

  4. O.A. Gerasko D.G. Samsonenko V.P. Fedin (2002) Russ. Chem. Rev 71 741 Occurrence Handle1:CAS:528:DC%2BD3sXjsFCksLY%3D Occurrence Handle10.1070/RC2002v071n09ABEH000748

    Article  CAS  Google Scholar 

  5. K.A. Kellersberger J.D. Anderson S.M. Ward K.E. Krakowiak D.V. Dearden (2001) J. Am. Chem. Soc 123 11316 Occurrence Handle10.1021/ja017031u Occurrence Handle1:CAS:528:DC%2BD3MXns1Oiur8%3D

    Article  CAS  Google Scholar 

  6. M. El Haouaj M. Luhmer Y.H. Ko K. Kim K. Bartik (2001) J. Chem. Soc. Perkin Trans 2 804

    Google Scholar 

  7. A. Flinn G.C. Hough J.F. Stoddart D.J. Williams (1992) Angew. Chem. Int. Ed. Engl 31 1475 Occurrence Handle10.1002/anie.199214751

    Article  Google Scholar 

  8. J. Kim I.-S Jung S.-Y. Kim E. Lee J.-K. Kang S. Sakamoto K. Yamaguchi K. Kim (2000) J. Am. Chem. Soc 122 540 Occurrence Handle1:CAS:528:DC%2BD3cXhs1Gjtw%3D%3D

    CAS  Google Scholar 

  9. J. Zhao H.-J. Kim J. Oh S.-Y. Kim J.W. Lee S. Sakamoto K. Yamaguchi K. Kim (2001) Angew. Chem. Int. Ed 40 4233 Occurrence Handle1:CAS:528:DC%2BD3MXovFeisLs%3D

    CAS  Google Scholar 

  10. K. Jansen H.-J. Buschmann A. Wego D. Döpp C. Mayer H.-J. Drexler H.-J. Holdt E. Schollmeyer (2001) J. Incl. Phenom 39 357 Occurrence Handle1:CAS:528:DC%2BD3MXktVWruro%3D

    CAS  Google Scholar 

  11. A. Day A.P. Arnold R.J. Blanch B. Snushall (2001) J. Org. Chem 66 8094 Occurrence Handle10.1021/jo015897c Occurrence Handle1:CAS:528:DC%2BD3MXotV2lurw%3D

    Article  CAS  Google Scholar 

  12. A.I. Day R.J. Blanch A.P. Arnold S. Lorenzo G.R. Lewis I. Dance (2002) Angew. Chem. Int. Ed 41 275 Occurrence Handle10.1002/1521-3773(20020118)41:2<275::AID-ANIE275>3.0.CO;2-M Occurrence Handle1:CAS:528:DC%2BD38XhtVyisbY%3D

    Article  CAS  Google Scholar 

  13. C. Marquez R.R. Hudgins W. Nau (2004) J. Am. Chem. Soc 126 5806 Occurrence Handle1:CAS:528:DC%2BD2cXivFSktb4%3D

    CAS  Google Scholar 

  14. K.S. Oh J. Yoon S. Kim (2001) J. Phys. Chem. B 105 9726 Occurrence Handle10.1021/jp011919n Occurrence Handle1:CAS:528:DC%2BD3MXmsFegur0%3D

    Article  CAS  Google Scholar 

  15. S. Immel, J. Brickmann, and F.W. Lichtenthaler: Liebigs Ann.Chem. , 929 (1995).

  16. F.W. Lichtenthaler S. Immel (1996) Starch/Stärke 48 145 Occurrence Handle1:CAS:528:DyaK28Xislyms7w%3D

    CAS  Google Scholar 

  17. M.J. Frisch G.W. Trucks H.B. Schlegel G.E. Scuseria M.A. Robb J.R. Cheeseman J.A. Montgomery SuffixJr. T. Vreven K.N. Kudin J.C. Burant J.M. Millam S.S. Iyengar J. Tomasi V. Barone B. Mennucci M. Cossi G. Scalmani N. Rega G.A. Petersson H. Nakatsuji M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai M. Klene X. Li J.E. Knox H.P. Hratchian J. B. Cross C. Adamo J. Jaramillo R. Gomperts R.E. Stratmann O. Yazyev A.J. Austin R. Cammi C. Pomelli J.W. Ochterski P.Y. Ayala K. Morokuma G.A. Voth P. Salvador J.J. Dannenberg V.G. Zakrzewski S. Dapprich A.D. Daniels M.C. Strain O. Farkas D.K. Malick A.D. Rabuck K. Raghavachari J.B. Foresman J.V. Ortiz Q. Cui A.G. Baboul S. Clifford J. Cioslowski B.B. Stefanov G. Liu A. Liashenko P. Piskorz I. Komaromi R.L. Martin D.J. Fox T. Keith M.A. Al-Laham C.Y. Peng A. Nanayakkara M. Challacombe P.M. W. Gill B. Johnson W. Chen M.W. Wong C. Gonzalez J.A. Pople (2003) Gaussian 03, Revision B.05 Gaussian Inc. Pittsburgh PA

    Google Scholar 

  18. GaussView 3, Gaussian, Inc., Pittsburgh PA (2003)

  19. C. Lee W. Yang R.G. Parr (1988) Phys. Rev. B 37 785 Occurrence Handle1:CAS:528:DyaL1cXktFWrtbw%3D

    CAS  Google Scholar 

  20. A.D Becke (1993) J. Chem. Phys 98 5648 Occurrence Handle1:CAS:528:DyaK3sXisVWgtrw%3D

    CAS  Google Scholar 

  21. J.R. Cheeseman G.W. Trucks T.A. Keith M.J. Frisch (1996) J. Chem. Phys 104 5497 Occurrence Handle10.1063/1.471789 Occurrence Handle1:CAS:528:DyaK28XitFaqtbo%3D

    Article  CAS  Google Scholar 

  22. J.B. Foresman Æ. Frisch (1996) Exploring Chemistry with Electronic Structure Methods Gaussian Inc Pittsburgh PA

    Google Scholar 

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Authors and Affiliations

  1. Deutsches Textilforschungszentrum Nord-West e.V., Adlerstr. 1, D-47798, Krefeld, Germany

    H.-J. Buschmann, A. Wego & E. Schollmeyer

  2. Department of Applied Natural Sciences, University of Applied Sciences Gelsenkirchen, August-Schmidt-Ring 10, D-45665, Recklinghausen, Germany

    A. Zielesny

Authors
  1. H.-J. Buschmann
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  2. A. Wego
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  3. A. Zielesny
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  4. E. Schollmeyer
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Correspondence to A. Zielesny.

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Buschmann, HJ., Wego, A., Zielesny, A. et al. Structure, Electronic Properties and NMR-Shielding of Cucurbit[n]urils. J Incl Phenom Macrocycl Chem 54, 85–88 (2006). https://doi.org/10.1007/s10847-005-4602-2

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  • DOI: https://doi.org/10.1007/s10847-005-4602-2

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