{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,11]],"date-time":"2025-11-11T12:52:12Z","timestamp":1762865532989},"reference-count":46,"publisher":"American Chemical Society (ACS)","issue":"23","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Phys. Chem. A"],"published-print":{"date-parts":[[2009,6,11]]},"DOI":"10.1021\/jp900089t","type":"journal-article","created":{"date-parts":[[2009,5,18]],"date-time":"2009-05-18T15:09:22Z","timestamp":1242659362000},"page":"6524-6530","source":"Crossref","is-referenced-by-count":5,"title":["Energetics of <i>tert<\/i>-Butoxyl Addition Reaction to Norbornadiene: A Method for Estimating the \u03c0-Bond Strength of a Carbon\u2212Carbon Double Bond"],"prefix":"10.1021","volume":"113","author":[{"given":"Paulo M.","family":"Nunes","sequence":"first","affiliation":[{"name":"Centro de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal, Grupo de F\u00edsica Matem\u00e1tica da Universidade de Lisboa, Av. Professor Gama Pinto, 2, 1649-003 Lisboa, Portugal, Instituto de Tecnologia Qu\u00edmica e Biol\u00f3gica, Universidade Nova de Lisboa, Av. da Rep\u00fablica, 2780-157 Oeiras, Portugal, and Institute for Biotechnology and Bioengineering, Centro de Biomedicina Molecular e Estrutural, Universidade do Algarve, Campus de Gambelas, 8005-139 Faro,..."}]},{"given":"S\u00edlvia G.","family":"Est\u00e1cio","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal, Grupo de F\u00edsica Matem\u00e1tica da Universidade de Lisboa, Av. Professor Gama Pinto, 2, 1649-003 Lisboa, Portugal, Instituto de Tecnologia Qu\u00edmica e Biol\u00f3gica, Universidade Nova de Lisboa, Av. da Rep\u00fablica, 2780-157 Oeiras, Portugal, and Institute for Biotechnology and Bioengineering, Centro de Biomedicina Molecular e Estrutural, Universidade do Algarve, Campus de Gambelas, 8005-139 Faro,..."}]},{"given":"Gustavo T.","family":"Lopes","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal, Grupo de F\u00edsica Matem\u00e1tica da Universidade de Lisboa, Av. Professor Gama Pinto, 2, 1649-003 Lisboa, Portugal, Instituto de Tecnologia Qu\u00edmica e Biol\u00f3gica, Universidade Nova de Lisboa, Av. da Rep\u00fablica, 2780-157 Oeiras, Portugal, and Institute for Biotechnology and Bioengineering, Centro de Biomedicina Molecular e Estrutural, Universidade do Algarve, Campus de Gambelas, 8005-139 Faro,..."}]},{"given":"Filipe","family":"Agapito","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal, Grupo de F\u00edsica Matem\u00e1tica da Universidade de Lisboa, Av. Professor Gama Pinto, 2, 1649-003 Lisboa, Portugal, Instituto de Tecnologia Qu\u00edmica e Biol\u00f3gica, Universidade Nova de Lisboa, Av. da Rep\u00fablica, 2780-157 Oeiras, Portugal, and Institute for Biotechnology and Bioengineering, Centro de Biomedicina Molecular e Estrutural, Universidade do Algarve, Campus de Gambelas, 8005-139 Faro,..."}]},{"given":"Rui C.","family":"Santos","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal, Grupo de F\u00edsica Matem\u00e1tica da Universidade de Lisboa, Av. Professor Gama Pinto, 2, 1649-003 Lisboa, Portugal, Instituto de Tecnologia Qu\u00edmica e Biol\u00f3gica, Universidade Nova de Lisboa, Av. da Rep\u00fablica, 2780-157 Oeiras, Portugal, and Institute for Biotechnology and Bioengineering, Centro de Biomedicina Molecular e Estrutural, Universidade do Algarve, Campus de Gambelas, 8005-139 Faro,..."}]},{"given":"Benedito J.","family":"Costa Cabral","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal, Grupo de F\u00edsica Matem\u00e1tica da Universidade de Lisboa, Av. Professor Gama Pinto, 2, 1649-003 Lisboa, Portugal, Instituto de Tecnologia Qu\u00edmica e Biol\u00f3gica, Universidade Nova de Lisboa, Av. da Rep\u00fablica, 2780-157 Oeiras, Portugal, and Institute for Biotechnology and Bioengineering, Centro de Biomedicina Molecular e Estrutural, Universidade do Algarve, Campus de Gambelas, 8005-139 Faro,..."}]},{"given":"Rui M.","family":"Borges dos Santos","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal, Grupo de F\u00edsica Matem\u00e1tica da Universidade de Lisboa, Av. Professor Gama Pinto, 2, 1649-003 Lisboa, Portugal, Instituto de Tecnologia Qu\u00edmica e Biol\u00f3gica, Universidade Nova de Lisboa, Av. da Rep\u00fablica, 2780-157 Oeiras, Portugal, and Institute for Biotechnology and Bioengineering, Centro de Biomedicina Molecular e Estrutural, Universidade do Algarve, Campus de Gambelas, 8005-139 Faro,..."}]},{"given":"Jos\u00e9 A.","family":"Martinho Sim\u00f5es","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal, Grupo de F\u00edsica Matem\u00e1tica da Universidade de Lisboa, Av. Professor Gama Pinto, 2, 1649-003 Lisboa, Portugal, Instituto de Tecnologia Qu\u00edmica e Biol\u00f3gica, Universidade Nova de Lisboa, Av. da Rep\u00fablica, 2780-157 Oeiras, Portugal, and Institute for Biotechnology and Bioengineering, Centro de Biomedicina Molecular e Estrutural, Universidade do Algarve, Campus de Gambelas, 8005-139 Faro,..."}]}],"member":"316","published-online":{"date-parts":[[2009,5,18]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"crossref","first-page":"748","DOI":"10.1021\/cr040077w","volume":"107","author":"Cheng Z.","year":"2007","journal-title":"Chem. Rev."},{"key":"ref2\/cit2","doi-asserted-by":"crossref","first-page":"1618","DOI":"10.1021\/jp066973o","volume":"111","author":"Peeters J.","year":"2007","journal-title":"J. Phys. Chem. A"},{"key":"ref3\/cit3","doi-asserted-by":"crossref","first-page":"778","DOI":"10.1021\/ed055p778","volume":"55","author":"Miller S. I.","year":"1978","journal-title":"J. Chem. Educ."},{"key":"ref4\/cit4","doi-asserted-by":"crossref","first-page":"6750","DOI":"10.1021\/ja00018a005","volume":"113","author":"Nicolaides A.","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5","doi-asserted-by":"crossref","first-page":"4444","DOI":"10.1021\/ja036309a","volume":"126","author":"Bach R. D.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1111\/j.1751-1097.1979.tb09258.x","volume":"29","author":"Small R. D.","year":"1979","journal-title":"Photochem. Photobiol."},{"key":"ref7\/cit7","doi-asserted-by":"crossref","first-page":"5106","DOI":"10.1021\/ja00383a018","volume":"104","author":"Wong P. C.","year":"1982","journal-title":"J. Am. Chem. Soc."},{"key":"ref8\/cit8","doi-asserted-by":"crossref","first-page":"2327","DOI":"10.1021\/jo00324a023","volume":"46","author":"Wong P. C.","year":"1981","journal-title":"J. Org. Chem."},{"key":"ref9\/cit9","doi-asserted-by":"crossref","first-page":"597","DOI":"10.1006\/jcht.1995.0061","volume":"27","author":"Diogo H. P.","year":"1995","journal-title":"J. Chem. Thermodyn."},{"key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"294","DOI":"10.1002\/anie.199402941","volume":"33","author":"Peters K. S.","year":"1994","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref11\/cit11","doi-asserted-by":"crossref","first-page":"1381","DOI":"10.1021\/cr00014a007","volume":"92","author":"Braslavsky S. E.","year":"1992","journal-title":"Chem. Rev."},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"1483","DOI":"10.1006\/jcht.1999.0513","volume":"31","author":"Borges dos Santos R. M.","year":"1999","journal-title":"J. Chem. Thermodyn."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"5130","DOI":"10.1021\/jp060325n","volume":"110","author":"Nunes P. M.","year":"2006","journal-title":"J. Phys. Chem. A"},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/j.tca.2003.10.027","volume":"420","author":"Correia C. F.","year":"2004","journal-title":"Thermochim. Acta"},{"key":"ref15\/cit15","volume-title":"Sound Analysis","year":"1999"},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"2598","DOI":"10.1063\/1.470985","volume":"104","author":"Ochterski J. W.","year":"1996","journal-title":"J. Chem. Phys."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"2822","DOI":"10.1063\/1.477924","volume":"110","author":"Montgomery J. A.","year":"1999","journal-title":"J. Chem. Phys."},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"6532","DOI":"10.1063\/1.481224","volume":"112","author":"Montgomery J. A.","year":"2000","journal-title":"J. Chem. Phys."},{"key":"ref19\/cit19","first-page":"35","volume":"14","author":"Cizek J.","year":"1969","journal-title":"Adv. Chem. Phys."},{"key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"5968","DOI":"10.1063\/1.453520","volume":"87","author":"Pople J. A.","year":"1987","journal-title":"J. Chem. Phys."},{"key":"ref21\/cit21","doi-asserted-by":"crossref","first-page":"4244","DOI":"10.1063\/1.439657","volume":"72","author":"Krishnam R.","year":"1980","journal-title":"J. Chem. Phys."},{"key":"ref22\/cit22","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1016\/S0009-2614(98)00866-5","volume":"294","author":"Truhlar D. G.","year":"1998","journal-title":"Chem. Phys. Lett."},{"key":"ref23\/cit23","doi-asserted-by":"crossref","first-page":"9736","DOI":"10.1021\/jp011132x","volume":"105","author":"Byrd E. F. C.","year":"2001","journal-title":"J. Phys. Chem. A"},{"key":"ref24\/cit24","volume-title":"Gaussian 03","author":"Frisch M. J.","year":"2004"},{"key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1021\/ja00027a050","volume":"114","author":"Hung R. R.","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ref26\/cit26","doi-asserted-by":"crossref","first-page":"841","DOI":"10.1002\/anie.198008413","volume":"19","author":"le Noble W. J.","year":"1980","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref27\/cit27","unstructured":"It should be noted that even if this estimate is wrong by 50%, the variation in the final value ofDH\u03c0calculated through eq8is only ca. 3 kJ mol\u22121."},{"key":"ref28\/cit28","doi-asserted-by":"crossref","first-page":"8737","DOI":"10.1021\/ja00139a006","volume":"117","author":"Wayner D. D. M.","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"ref29\/cit29","volume-title":"Organic Solvents. Physical Properties and Methods of Purification","author":"Riddick J. A.","year":"1986","edition":"4"},{"key":"ref30\/cit30","doi-asserted-by":"crossref","first-page":"2744","DOI":"10.1021\/j100062a009","volume":"98","author":"Berkowitz J.","year":"1994","journal-title":"J. Phys. Chem."},{"key":"ref31\/cit31","volume-title":"Thermochemical Data and Structures of Organic Compounds","author":"Pedley J. B.","year":"1994"},{"key":"ref32\/cit32","doi-asserted-by":"crossref","first-page":"573","DOI":"10.1063\/1.1724828","volume":"34","author":"Ruscic B.","year":"2005","journal-title":"J. Phys. Chem. Ref. Data"},{"key":"ref33\/cit33","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1021\/ar020230d","volume":"36","author":"Blanksby S. J.","year":"2003","journal-title":"Acc. Chem. Res."},{"key":"ref35\/cit35","doi-asserted-by":"crossref","first-page":"315","DOI":"10.1063\/1.1741959","volume":"23","author":"Douglas J. E.","year":"1955","journal-title":"J. Chem. Phys."},{"key":"ref36\/cit36","unstructured":"\u0394rH2\u00b0, (gas)\/2 = \u0394rH2\u00b0(sln)\/2 + \u0394slnH\u00b0(C7H9) + \u0394slnH\u00b0(t-BuO\u2022) \u2212 \u0394slnH\u00b0(C7H9\u2212O-t-Bu) but the solvation terms in benzene should cancel out. As shown below, theDH\u03c0value for norbornadiene obtained in the gas phase using the addition reaction of methoxyl radical (Table1) and theDH\u03c0derived using eq8are identical, suggesting that this assumption is correct."},{"key":"ref37\/cit37","doi-asserted-by":"crossref","first-page":"3158","DOI":"10.1021\/jo020650g","volume":"68","author":"Matsunaga N.","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref38\/cit38","doi-asserted-by":"crossref","first-page":"1613","DOI":"10.1021\/ol800333q","volume":"10","author":"Nunes P. M.","year":"2008","journal-title":"Org. Lett."},{"key":"ref39\/cit39","volume-title":"NIST Chemistry WebBook","author":"Afeefy H. Y.","year":"2005"},{"key":"ref40\/cit40","volume-title":"Thermochemistry of Organic and Organometallic Compounds","author":"Cox J. D.","year":"1970"},{"key":"ref41\/cit41","doi-asserted-by":"crossref","first-page":"6213","DOI":"10.1021\/jo800690m","volume":"73","author":"Agapito F.","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref42\/cit42","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1063\/1.1996609","volume":"35","author":"Leal J. P.","year":"2006","journal-title":"J. Phys. Chem. Ref. Data"},{"key":"ref43\/cit43","doi-asserted-by":"crossref","first-page":"3129","DOI":"10.1021\/jo035306d","volume":"69","author":"Feng Y.","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref44\/cit44","doi-asserted-by":"crossref","first-page":"9947","DOI":"10.1021\/jp020594n","volume":"106","author":"Ervin K. M.","year":"2002","journal-title":"J. Phys. Chem. A"},{"key":"ref45\/cit45","volume-title":"The Chemical Thermodynamics of Organic Compounds","author":"Stull D. R.","year":"1969"},{"key":"ref46\/cit46","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/0022-328X(96)06193-1","volume":"518","author":"Minas da Piedade M. E.","year":"1996","journal-title":"J. Organomet. Chem."},{"key":"ref47\/cit47","doi-asserted-by":"crossref","first-page":"6393","DOI":"10.1021\/ja00411a021","volume":"103","author":"Encinas M. V.","year":"1981","journal-title":"J. Am. Chem. 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