Skip to main content
SpringerLink
Log in

Detours for Reaching at New Germylenes, Silylenes, Carbenes, and Carbenogermylenes through Substituted Cyclopropenylidenes at Ab initio and DFT Levels

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

Summary.

Heavier atom containing X 2SiC2, and X 2GeC2 cyclopropenylidenes transform into new silylenes, germylenes, and carbenogermylenes at DFT and ab initio levels (X = H, CN, NH2, and OMe). The number of transformations or rearrangements appear roughly proportional to the covalent radii of the group 14 elements (Ge > Si > C).

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

  • Y Yamaguchi HF Schaefer SuffixIII (1996) J Phys Chem 100 7911 Occurrence Handle10.1021/jp953150i Occurrence Handle1:CAS:528:DyaK28XitlOltb4%3D

    Article  CAS  Google Scholar 

  • CD Sherrill TJV Huis Y Yamaguchi HF Schaefer SuffixIII (1997) J Mol Struct (THEOCHEM) 400 39

    Google Scholar 

  • CD Sherrill ML Leininger TJV Huis HF Schaefer SuffixIII (1998) J Phys Chem 108 1040 Occurrence Handle10.1063/1.475465 Occurrence Handle1:CAS:528:DyaK1cXitVSnsg%3D%3D

    Article  CAS  Google Scholar 

  • VM Garcia O Castell M Reguero R Caballol (1996) Mol Phys 87 1395 Occurrence Handle1:CAS:528:DyaK28XivValtr4%3D

    CAS  Google Scholar 

  • D Das SL Whittenburg (1999) J Mol Struct (THEOCHEM) 92 175 Occurrence Handle10.1016/S0166-1280(99)00169-4

    Article  Google Scholar 

  • M Schwartz P Marshall (1999) J Phys Chem A 103 7900 Occurrence Handle10.1021/jp9919213 Occurrence Handle1:CAS:528:DyaK1MXlslGntrY%3D

    Article  CAS  Google Scholar 

  • K Sendt GB Bacskay (2000) J Chem Phys 112 2227 Occurrence Handle10.1063/1.481592 Occurrence Handle1:CAS:528:DC%2BD3cXnsFaisA%3D%3D

    Article  CAS  Google Scholar 

  • RL Schwartz GE Davico TM Ramond WC Lineberger (1999) J Phys Chem A 103 8213 Occurrence Handle10.1021/jp992214c Occurrence Handle1:CAS:528:DyaK1MXmtF2rsLo%3D

    Article  CAS  Google Scholar 

  • CJ Barden HF Schaefer SuffixIII (2000) J Chem Phys 112 6515 Occurrence Handle10.1063/1.481601 Occurrence Handle1:CAS:528:DC%2BD3cXitlSrsLk%3D

    Article  CAS  Google Scholar 

  • EPF Lee JM Dyke TG Wright (2000) Chem Phys Lett 326 143 Occurrence Handle10.1016/S0009-2614(00)00737-5 Occurrence Handle1:CAS:528:DC%2BD3cXltleksLo%3D

    Article  CAS  Google Scholar 

  • B Hajgato HMT Nguyen T Veszpremi MT Nguyen (2000) Phys Chem Chem Phys 2 5041 Occurrence Handle10.1039/b005208f Occurrence Handle1:CAS:528:DC%2BD3cXnvVynsbo%3D

    Article  CAS  Google Scholar 

  • M Hargittai G Schultz P Schwerdtfeger MJ Seth (2001) Struct Chem 12 377 Occurrence Handle10.1023/A:1011960320787 Occurrence Handle1:CAS:528:DC%2BD3MXot12ks7g%3D

    Article  CAS  Google Scholar 

  • R Vargas M Galvan A Vela (1998) J Phys Chem A 102 3134 Occurrence Handle10.1021/jp972984t Occurrence Handle1:CAS:528:DyaK1cXivVektLY%3D

    Article  CAS  Google Scholar 

  • PJ Stang (1978) Chem Rev 78 38347 Occurrence Handle10.1021/cr60314a003

    Article  Google Scholar 

  • P Thaddeus JM Vrtilek CA Gottlieb (1985) Astrophys J 299 L63 Occurrence Handle10.1086/184581 Occurrence Handle1:CAS:528:DyaL28XlvV2huw%3D%3D

    Article  CAS  Google Scholar 

  • J Cernicharo CA Gottlieb M Guelin TC Killian G Paubert P Thaddeus JM Vrtilek (1991) Astrophys J 368 L39 Occurrence Handle10.1086/185943 Occurrence Handle1:CAS:528:DyaK3MXhslCgt7c%3D

    Article  CAS  Google Scholar 

  • JM Vrtilek CA Gottlieb M Guelin TC Killian G Paubert P Thaddeus (1990) Astrophys J 364 L53 Occurrence Handle10.1086/185873 Occurrence Handle1:CAS:528:DyaK3MXptV2htA%3D%3D

    Article  CAS  Google Scholar 

  • DJ DeFrees AD McLean (1986) Astrophys J 308 L31 Occurrence Handle10.1086/184738 Occurrence Handle1:CAS:528:DyaL28Xls1WlsLo%3D

    Article  CAS  Google Scholar 

  • DL Cooper SC Murphy (1988) Astrophys J 333 482 Occurrence Handle10.1086/166761 Occurrence Handle1:CAS:528:DyaL1MXhtlyitA%3D%3D

    Article  CAS  Google Scholar 

  • HP Reisenauer G Maier A Reimann RW Hoffmann (1984) Angew Chem Int Ed 96 596 Occurrence Handle10.1002/ange.19840960811 Occurrence Handle1:CAS:528:DyaL2cXlslSksbc%3D

    Article  CAS  Google Scholar 

  • MZ Kassaee BN Haerizade S Arshadi (2003) J Mol Struct (THEOCHEM) 639 187 Occurrence Handle10.1016/j.theochem.2003.08.008 Occurrence Handle1:CAS:528:DC%2BD3sXosVKrtr0%3D

    Article  CAS  Google Scholar 

  • MZ Kassaee SZ Sayyed-Alangi Z Hossaini (2004) J Mol Struct (THEOCHEM) 676 7 Occurrence Handle10.1016/j.theochem.2004.01.008 Occurrence Handle1:CAS:528:DC%2BD2cXjsVCku78%3D

    Article  CAS  Google Scholar 

  • Y Apeloig R Pauncz M Karni R West W Steiner D Chapman (2003) Organometallics 22 3250 Occurrence Handle10.1021/om0302591 Occurrence Handle1:CAS:528:DC%2BD3sXltFKqu70%3D

    Article  CAS  Google Scholar 

  • MZ Kassaee SM Musavi M Ghambarian MR Khalili Zanjani (2006) J Organomet Chem 691 2933 Occurrence Handle10.1016/j.jorganchem.2006.02.038 Occurrence Handle1:CAS:528:DC%2BD28XkvF2ru74%3D

    Article  CAS  Google Scholar 

  • MZ Kassaee SM Musavi S Soleimani-Amiri M Ghambarian (2006) Heteroatom Chemistry 17 619 Occurrence Handle10.1002/hc.20204 Occurrence Handle1:CAS:528:DC%2BD28Xht1yksLnJ

    Article  CAS  Google Scholar 

  • C Barrientos P Redondo A Largo (2000) J Phys Chem A 104 11541 Occurrence Handle10.1021/jp002454o Occurrence Handle1:CAS:528:DC%2BD3cXnvVKisbs%3D

    Article  CAS  Google Scholar 

  • C Barrientos A Cimas A Largo (2001) J Phys Chem A 105 6724 Occurrence Handle10.1021/jp010263v Occurrence Handle1:CAS:528:DC%2BD3MXktlalurw%3D

    Article  CAS  Google Scholar 

  • A Largo JR Redondo P Redondo (2000) J Mol Struct (THEOCHEM) 505 221 Occurrence Handle10.1016/S0166-1280(99)00377-2

    Article  Google Scholar 

  • Maier G, Reisenauer HP, Egenolf H, Meudt A Eur (1998) J Org Chem 1297

  • J Kalcher P Skurski J Simons (2007) J Phys Chem A 111 401 Occurrence Handle10.1021/jp066551e Occurrence Handle1:CAS:528:DC%2BD28Xhtlekt7jF

    Article  CAS  Google Scholar 

  • Schriver GW, Fink MJ, Gordon MS (1987) Organometallics 1977

  • MZ Kassaee SM Musavi F Buazar (2006) Chemical Monthly 137 1385 Occurrence Handle10.1007/s00706-006-0539-4 Occurrence Handle1:CAS:528:DC%2BD28XhtFKgu7%2FJ

    Article  CAS  Google Scholar 

  • BA Hess (Eds) (2003) Relativistic Effects in Heavy-Element Chemistry and Physics Wiley New York

    Google Scholar 

  • (a) Kapp J, Remko M, Schleyer PVR (1996) J Am Chem Soc 118: 5745; (b) Kapp J, Remko M, Schleyer PVR (1997) Inorg Chem 36: 4241

  • (a) Kapp J, Remko M, Schleyer PVR (1993) J Am Chem Soc 115: 1061; (b) Kutzelnigg W (1984) Angew Chem Int Ed Engl 23: 272

  • JC Barthelat G Trinquier G Bertrand (1979) J Am Chem Soc 101 3785 Occurrence Handle10.1021/ja00508a015 Occurrence Handle1:CAS:528:DyaE1MXltVOmt7o%3D

    Article  CAS  Google Scholar 

  • Y Apeloig M Karni (1984) J Am Chem Soc 106 6676 Occurrence Handle10.1021/ja00334a036 Occurrence Handle1:CAS:528:DyaL2cXlvFajtrw%3D

    Article  CAS  Google Scholar 

  • (a) Schmidt MW, Truong PN, Gordon MS (1987) J Am Chem Soc 109: 5217; (b) Schleyer PVR, Kost D (1988) J Am Chem Soc 110: 2105

  • Brook AG, Abdesaken F, Gutekunst B, Gutekunst G, Kallury RK (1981) J Chem Soc Chem Commun 191

  • T Enyo A Nicolaides H Tomioka (2002) J Org Chem 67 5578 Occurrence Handle10.1021/jo025877q Occurrence Handle1:CAS:528:DC%2BD38Xlt1Cjtro%3D

    Article  CAS  Google Scholar 

  • A Nicolaides T Nakayama K Yamazaki H Tomioka S Koseki LL Stracener RJ McMahon (1999) J Am Chem Soc 121 10563 Occurrence Handle10.1021/ja9913636 Occurrence Handle1:CAS:528:DyaK1MXmvFCktLo%3D

    Article  CAS  Google Scholar 

  • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG Jr, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millan JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelly C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (1998) 98, Gaussian Inc., Revision A7, Pittsburgh, PA

  • R McWeeny G Dierksen (1968) J Chem Phys 49 4852 Occurrence Handle10.1063/1.1669970 Occurrence Handle1:CAS:528:DyaF1MXktVOgsw%3D%3D

    Article  CAS  Google Scholar 

  • AD Becke (1996) J Chem Phys 104 1040 Occurrence Handle10.1063/1.470829 Occurrence Handle1:CAS:528:DyaK28Xls1Olsw%3D%3D

    Article  CAS  Google Scholar 

  • C Adamo V Barone (1997) Chem Phys Lett 274 242 Occurrence Handle10.1016/S0009-2614(97)00651-9 Occurrence Handle1:CAS:528:DyaK2sXkslGitbg%3D

    Article  CAS  Google Scholar 

  • ER Davidson (1996) Chem Phys Lett 220 514 Occurrence Handle10.1016/0009-2614(96)00917-7

    Article  Google Scholar 

  • S Saebo J Almlof (1989) Chem Phys Lett 154 83 Occurrence Handle10.1016/0009-2614(89)87442-1 Occurrence Handle1:CAS:528:DyaL1MXhsVWktrg%3D

    Article  CAS  Google Scholar 

  • JA Pople R Krishnan (1978) J Int Quant Chem 14 91 Occurrence Handle10.1002/qua.560140109

    Article  Google Scholar 

  • R Krishnan MJ Frisch JA Pople (1980) J Chem Phys 72 4244 Occurrence Handle10.1063/1.439657 Occurrence Handle1:CAS:528:DyaL3cXksFCgt7c%3D

    Article  CAS  Google Scholar 

  • JA Pople M Head-Gordon K Raghavachari (1987) J Chem Phys 87 5968 Occurrence Handle10.1063/1.453520 Occurrence Handle1:CAS:528:DyaL1cXislSqsw%3D%3D

    Article  CAS  Google Scholar 

  • RF Hout BA Levi WJ Heher (1985) J Comput Chem 82 234

    Google Scholar 

  • DJ Defrees AD McLean (1985) J Chem Phys 82 333 Occurrence Handle10.1063/1.448805 Occurrence Handle1:CAS:528:DyaL2MXhtVamtbo%3D

    Article  CAS  Google Scholar 

  • JE Carpenter F Weinhold (1988) J Mol Struct (THEOCHEM) 41 169

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modares University, Tehran, Iran

    Mohammad Z. Kassaee & Elaheh Motamedi

  2. Department of Marine Chemistry, Khorramshahr University of Nautical Sciences and Technologies, Khorramshahr, Iran

    Foad Buazar

  3. Department of Chemistry, Hormozgan University, Bandar Abbas, Iran

    Seyed M. Musavi

Authors
  1. Mohammad Z. Kassaee
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Foad Buazar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Seyed M. Musavi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Elaheh Motamedi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohammad Z. Kassaee.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kassaee, M., Buazar, F., Musavi, S. et al. Detours for Reaching at New Germylenes, Silylenes, Carbenes, and Carbenogermylenes through Substituted Cyclopropenylidenes at Ab initio and DFT Levels. Monatsh. Chem. 138, 833–848 (2007). https://doi.org/10.1007/s00706-007-0682-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-007-0682-6

Search

Navigation