메뉴 건너뛰기




Volumn 13, Issue 5, 2007, Pages 367-372

Letter: Silver mediated ester bond formation in the gas phase: Substrate structure is important

Author keywords

Allyl iodide; C I bond activation; C O bond formation; DFT calculations; Electrospray; Gas phase ion molecule reactions; Methyl iodide; Silver acetate cluster cations; Silver iodide cluster cations; Tandem mass spectrometry

Indexed keywords

ACETIC ACID DERIVATIVE; ESTER; IODIDE; SILVER DERIVATIVE;

EID: 39749124960     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.888     Document Type: Article
Times cited : (6)

References (24)
  • 1
    • 0013272402 scopus 로고    scopus 로고
    • A. Togni and H. Grützmacher, Eds, Wiley-VCH, Weinheim, Germany
    • A. Togni and H. Grützmacher, (Eds), Catalytic Heterofunctionalization. Wiley-VCH, Weinheim, Germany (2001).
    • (2001) Catalytic Heterofunctionalization
  • 2
    • 0001686343 scopus 로고
    • Mercury in organic chemistry. V. Direct esterification of alkyl halides
    • doi: 10.1021/jo00939a025
    • R.C. Larock, "Mercury in organic chemistry. V. Direct esterification of alkyl halides", J. Org. Chem. 39, 3721 (1974). doi: 10.1021/jo00939a025
    • (1974) J. Org. Chem , vol.39 , pp. 3721
    • Larock, R.C.1
  • 3
    • 0001210767 scopus 로고
    • Substitution and rearrangement reactions of allylic compounds
    • For a review of the earlier literature see:, doi: 10.1021/cr50010a002
    • For a review of the earlier literature see: R.H. DeWolfe and W.G. Young, "Substitution and rearrangement reactions of allylic compounds", Chem. Rev. 56, 753 (1956). doi: 10.1021/cr50010a002
    • (1956) Chem. Rev , vol.56 , pp. 753
    • DeWolfe, R.H.1    Young, W.G.2
  • 4
    • 13444304419 scopus 로고    scopus 로고
    • + and its Mediation of C-C Bond Coupling of Allylbromide
    • doi: 10.1002/anie.200461328
    • + and its Mediation of C-C Bond Coupling of Allylbromide", Angew. Chem. Int. Ed. 44, 728 (2005). doi: 10.1002/anie.200461328
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 728
    • Khairallah, G.N.1    O'Hair, R.A.J.2
  • 6
    • 33645460222 scopus 로고    scopus 로고
    • The 3D Quadrupole Ion Trap Mass Spectrometer as a Complete Chemical Laboratory for Fundamental Gas Phase Studies of Metal Mediated Chemistry
    • doi: 10.1039/b516348j
    • R.A.J. O'Hair, "The 3D Quadrupole Ion Trap Mass Spectrometer as a Complete Chemical Laboratory for Fundamental Gas Phase Studies of Metal Mediated Chemistry", Chem. Commun. 1469 (2006). doi: 10.1039/b516348j
    • (2006) Chem. Commun , vol.1469
    • O'Hair, R.A.J.1
  • 7
    • 0035074189 scopus 로고    scopus 로고
    • Metal-assisted esterification: Glutaric acid-iron(II) complexes in the gas phase
    • For an example of gas-phase formation of esters see:, doi: 10.1002/rcm.254
    • For an example of gas-phase formation of esters see: Yong-III Lee, Sung-Chan Jo, W. Andy Tao and R.G. Cooks, "Metal-assisted esterification: glutaric acid-iron(II) complexes in the gas phase", Rapid Commun. Mass Spectrom. 15, 484 (2001). doi: 10.1002/rcm.254
    • (2001) Rapid Commun. Mass Spectrom , vol.15 , pp. 484
    • Lee, Y.-I.1    Jo, S.-C.2    Andy Tao, W.3    Cooks, R.G.4
  • 8
    • 0242669326 scopus 로고    scopus 로고
    • + in the Gas Phase
    • For other examples of metal mediated C-heteroatom bond formation see: a, doi: 10.1021/ja029791q
    • + in the Gas Phase", J Am. Chem. Soc. 125, 3676 (2003); doi: 10.1021/ja029791q
    • (2003) J Am. Chem. Soc , vol.125 , pp. 3676
    • Koszinowski, K.1    Schröder, D.2    Schwarz, H.3
  • 10
    • 39749141971 scopus 로고    scopus 로고
    • +, have been observed in a number of mass spectra of silver carboxylates:
    • +, have been observed in a number of mass spectra of silver carboxylates:
  • 11
    • 4244205953 scopus 로고
    • Mass spectrometric investigation of silver ion promoted carbon-carbon bond scission
    • doi: 10.1021/ic00192a051
    • (a) K.L. Busch, R.G. Cooks, R.A. Walton and K.V. Wood, "Mass spectrometric investigation of silver ion promoted carbon-carbon bond scission", Inorg. Chem. 23, 4093 (1984); doi: 10.1021/ic00192a051
    • (1984) Inorg. Chem , vol.23 , pp. 4093
    • Busch, K.L.1    Cooks, R.G.2    Walton, R.A.3    Wood, K.V.4
  • 13
    • 0001179848 scopus 로고
    • Silver(I) carboxylates. I. Mass spectra and low-frequency infrared spectra
    • (c) S.K. Adams, D.A. Edwards and R. Richards, "Silver(I) carboxylates. I. Mass spectra and low-frequency infrared spectra", Inorg. Chim. Acta 12, 163 (1975);
    • (1975) Inorg. Chim. Acta , vol.12 , pp. 163
    • Adams, S.K.1    Edwards, D.A.2    Richards, R.3
  • 14
    • 84989056589 scopus 로고
    • The mass spectra of some silver salts
    • doi: 10.1002/oms.1210161209
    • (d) G.D. Roberts and E.V. White, "The mass spectra of some silver salts", Org. Mass Spectrom. 16, 546 (1981). 14 doi: 10.1002/oms.1210161209
    • (1981) Org. Mass Spectrom , vol.16 , Issue.546 , pp. 14
    • Roberts, G.D.1    White, E.V.2
  • 15
    • 0037454325 scopus 로고    scopus 로고
    • Catalytic Gas Phase Oxidation of Methanol to Formaldehyde
    • doi: 10.1021/ja028839x
    • T. Waters, R.A.J. O'Hair and A.G. Wedd, "Catalytic Gas Phase Oxidation of Methanol to Formaldehyde", J. Am. Chem. Soc. 125, 3384 (2003). doi: 10.1021/ja028839x
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 3384
    • Waters, T.1    O'Hair, R.A.J.2    Wedd, A.G.3
  • 16
    • 0032237966 scopus 로고    scopus 로고
    • Estimation of effective ion temperatures in a quadrupole ion trap
    • doi: 10.1016/S1044-0305(98)00055-5
    • S. Gronert, "Estimation of effective ion temperatures in a quadrupole ion trap", J. Am. Soc. Mass Spectrom. 9, 845 (1998). doi: 10.1016/S1044-0305(98)00055-5
    • (1998) J. Am. Soc. Mass Spectrom , vol.9 , pp. 845
    • Gronert, S.1
  • 17
    • 39749196571 scopus 로고    scopus 로고
    • M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr, 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. Pomell, 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. Gonz
    • M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr, 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. Pomell, 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 and J.A. Pople, Gaussian_03. Gaussian, Inc., Pittsburgh, PA, USA (2003).
  • 18
    • 36549092018 scopus 로고
    • Energy-adjusted ab initio pseudopotentials for the first row transition elements
    • doi: 10.1063/1.452288
    • (a) M. Dolg, U. Wedig and H. Preuss, "Energy-adjusted ab initio pseudopotentials for the first row transition elements", J. Chem. Phys. 86, 866 (1987); doi: 10.1063/1.452288
    • (1987) J. Chem. Phys , vol.86 , pp. 866
    • Dolg, M.1    Wedig, U.2    Preuss, H.3
  • 19
    • 84944675147 scopus 로고
    • Ab initio energy-adjusted pseudopotentials for elements of groups 13-17
    • doi: 10.1080/002 68979300103121
    • (b) A. Bergner, M. Dolg, W. Kuechle, H. Stoll and H. Preuss, "Ab initio energy-adjusted pseudopotentials for elements of groups 13-17", Mol. Phys. 80, 1431 (1993). doi: 10.1080/002 68979300103121
    • (1993) Mol. Phys , vol.80 , pp. 1431
    • Bergner, A.1    Dolg, M.2    Kuechle, W.3    Stoll, H.4    Preuss, H.5
  • 20
    • 9144250275 scopus 로고    scopus 로고
    • B.K. Agrawal, S. Agrawal, P. Srivastava and S. Singh, Ab-initio Study of Small Silver Nanoclusters, J. Nanopart. Res. 6, 363 (2004).doi: 10.1023/B:NANO.0000046744.53994.4d
    • B.K. Agrawal, S. Agrawal, P. Srivastava and S. Singh, "Ab-initio Study of Small Silver Nanoclusters", J. Nanopart. Res. 6, 363 (2004).doi: 10.1023/B:NANO.0000046744.53994.4d
  • 21
    • 33645503120 scopus 로고    scopus 로고
    • The Simple Yet Elusive Crystal Structure of Silver Acetate and the Role of the Ag-Ag Bond in the Formation of Silver Nanoparticles during the Thermally Induced Reduction of Silver Carboxylates
    • doi: 10.1021/cm052657v
    • L.P. Olson, D.R. Whitcomb, M. Rajeswaran, T.N. Blanton and B. J. Stwertka, "The Simple Yet Elusive Crystal Structure of Silver Acetate and the Role of the Ag-Ag Bond in the Formation of Silver Nanoparticles during the Thermally Induced Reduction of Silver Carboxylates", Chem. Mater. 18, 1667 (2006). doi: 10.1021/cm052657v
    • (2006) Chem. Mater , vol.18 , pp. 1667
    • Olson, L.P.1    Whitcomb, D.R.2    Rajeswaran, M.3    Blanton, T.N.4    Stwertka, B.J.5
  • 24
    • 34547218001 scopus 로고    scopus 로고
    • Activation of the C-I and C-OH Bonds of 2-Iodoethanol by Gas Phase Silver Cluster Cations Yields Subvalent Silver-Iodide and -Hydroxide Cluster Cations
    • doi: 10.1039/b700132k
    • G.N. Khairallah and R.A.J. O'Hair, "Activation of the C-I and C-OH Bonds of 2-Iodoethanol by Gas Phase Silver Cluster Cations Yields Subvalent Silver-Iodide and -Hydroxide Cluster Cations", Dalton Trans. 3149 (2007). doi: 10.1039/b700132k
    • (2007) Dalton Trans , vol.3149
    • Khairallah, G.N.1    O'Hair, R.A.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.