Skip to main content
SpringerLink
Log in

DFT-calculated structure of protonated tetraphenyl p-tert-butylcalix[4]arene tetraketone

  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Using DFT calculations, two of the most probable structures (A, B) of the tetraphenyl p-tert-butylcalix[4]arene tetraketone·H3O+ cationic complex species were derived. The hydroxonium ion H3O+, placed in the coordination cavity formed by the calix[4]arene lower-rim groups, is bound by strong hydrogen bonds to the phenoxy oxygen atoms of the calix[4]arene ligand (structures A, B) and also to one carbonyl oxygen (structure B).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • V Böhmer (1995) Angew Chem 34 713 Occurrence Handle10.1002/anie.199507131

    Article  Google Scholar 

  • CD Gutsche (1998) Calixarenes Revisited The Royal Society of Chemistry Cambridge

    Google Scholar 

  • A Arduini A Pochini S Reverberi R Ungaro (1986) Tetrahedron 42 2089 Occurrence Handle10.1016/S0040-4020(01)87626-2 Occurrence Handle1:CAS:528:DyaL2sXitl2mtg%3D%3D

    Article  CAS  Google Scholar 

  • A Arduini E Ghidini A Pochini R Ungaro GD Andreetti G Calestani F Ugozzoli (1988) J Inclusion Phenom 6 119 Occurrence Handle10.1007/BF00663045 Occurrence Handle1:CAS:528:DyaL1cXlvVansrc%3D

    Article  CAS  Google Scholar 

  • F Arnaud-Neu EM Collins M Deasy G Ferguson SJ Harris B Kaitner AJ Lough MA McKervey E Marques BL Ruhl MJ Schwing-Weill EM Seward (1989) J Am Chem Soc 111 8681 Occurrence Handle10.1021/ja00205a018 Occurrence Handle1:CAS:528:DyaL1MXmtlWmtbg%3D

    Article  CAS  Google Scholar 

  • F Arnaud-Neu G Barrett SJ Harris M Owens MA McKervey MJ Schwing-Weill P Schwinté (1993) Inorg Chem 32 2644 Occurrence Handle10.1021/ic00064a013 Occurrence Handle1:CAS:528:DyaK3sXis1Wkt74%3D

    Article  CAS  Google Scholar 

  • K Ohto E Murakami T Shinohara K Shiratsuchi K Inoue M Iwasaki (1997) Anal Chim Acta 341 275 Occurrence Handle10.1016/S0003-2670(96)00555-7 Occurrence Handle1:CAS:528:DyaK2sXhsFKntbw%3D

    Article  CAS  Google Scholar 

  • Z Ye W He X Shi L Zhu (2001) J Coord Chem 54 105 Occurrence Handle10.1080/00958970108027147 Occurrence Handle1:CAS:528:DC%2BD3MXmsFKju7o%3D

    Article  CAS  Google Scholar 

  • AF Danil de Namor S Chahine D Kowalska EE Castellano OE Piro (2002) J Am Chem Soc 124 12824 Occurrence Handle10.1021/ja020764+ Occurrence Handle1:CAS:528:DC%2BD38XnsFGnu7w%3D

    Article  CAS  Google Scholar 

  • PM Marcos JR Ascenso MAP Segurado JLC Pereira (2002) J Inclusion Phenom 42 281 Occurrence Handle10.1023/A:1016083624362 Occurrence Handle1:CAS:528:DC%2BD38XkvVCntbc%3D

    Article  CAS  Google Scholar 

  • PM Marcos S Félix JR Ascenso MAP Segurado JLC Pereira P Khazaeli-Parsa V Hubscher-Bruder F Arnaud-Neu (2004) New J Chem 28 748 Occurrence Handle10.1039/b401423p Occurrence Handle1:CAS:528:DC%2BD2cXksV2gtb8%3D

    Article  CAS  Google Scholar 

  • E Makrlík P Vaňura (2006) Monatsh Chem 137 1185 Occurrence Handle10.1007/s00706-006-0523-z

    Article  Google Scholar 

  • J Dybal E Makrlík P Vaňura (2007) Monatsh Chem 138 541 Occurrence Handle10.1007/s00706-007-0646-x Occurrence Handle1:CAS:528:DC%2BD2sXlslCrt7w%3D

    Article  CAS  Google Scholar 

  • J Kříž J Dybal E Makrlík J Budka P Vaňura (2007) Monatsh Chem 138 735 Occurrence Handle10.1007/s00706-007-0677-3

    Article  Google Scholar 

  • J Dybal E Makrlík P Vaňura P Selucký (2007) Monatsh Chem 138 1239 Occurrence Handle10.1007/s00706-007-0731-1 Occurrence Handle1:CAS:528:DC%2BD2sXhtlKrtrfL

    Article  CAS  Google Scholar 

  • Dybal J, Makrlík E, Vaňura P, Budka J (2008) Monatsh Chem 139: (in press)

  • E Makrlík P Vaňura (1985) Talanta 32 423 Occurrence Handle10.1016/0039-9140(85)80110-7

    Article  Google Scholar 

  • Makrlík E, Budka J, Vaňura P, Dybal J (2008) Monatsh Chem 139: (in press)

  • 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

  • J Kříž J Dybal E Makrlík (2006) Biopolymers 82 536 Occurrence Handle10.1002/bip.20506

    Article  Google Scholar 

  • J Kříž J Dybal E Makrlík P Vaňura J Lang (2007) Supramol Chem 19 419 Occurrence Handle10.1080/10610270601089360

    Article  Google Scholar 

  • J Kříž J Dybal E Makrlík P Vaňura (2008) Supramol Chem 20 387 Occurrence Handle10.1080/10610270701278251

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic

    Jiří Dybal

  2. Faculty of Applied Sciences, University of West Bohemia, Pilsen, Czech Republic

    Emanuel Makrlík

  3. Institute of Chemical Technology, Prague, Czech Republic

    Jan Budka & Petr Vaňura

Authors
  1. Jiří Dybal
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Emanuel Makrlík
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jan Budka
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Petr Vaňura
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Emanuel Makrlík.

Additional information

Correspondence: Emanuel Makrlík, Faculty of Applied Sciences, University of West Bohemia, Pilsen, Czech Republic.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dybal, J., Makrlík, E., Budka, J. et al. DFT-calculated structure of protonated tetraphenyl p-tert-butylcalix[4]arene tetraketone. Monatsh Chem 139, 1353–1355 (2008). https://doi.org/10.1007/s00706-008-0938-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-008-0938-9

Keywords

Search

Navigation