{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T17:19:44Z","timestamp":1760548784545},"reference-count":41,"publisher":"American Chemical Society (ACS)","issue":"8","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Phys. Chem. A"],"published-print":{"date-parts":[[2009,2,26]]},"DOI":"10.1021\/jp8101354","type":"journal-article","created":{"date-parts":[[2009,1,26]],"date-time":"2009-01-26T15:28:57Z","timestamp":1232983737000},"page":"1628-1634","source":"Crossref","is-referenced-by-count":14,"title":["Theoretical Study on the Stability of Formylphenol and Formylaniline Compounds and Corresponding Radicals: O\u2212H or N\u2212H vs C\u2212H Bond Dissociation"],"prefix":"10.1021","volume":"113","author":[{"given":"Jos\u00e9 R. B.","family":"Gomes","sequence":"first","affiliation":[{"name":"CICECO, University of Aveiro, Campus Universit\u00e1rio de Santiago, P-3810-193 Aveiro, Portugal"}]}],"member":"316","published-online":{"date-parts":[[2009,1,26]]},"reference":[{"key":"ref1\/cit1","unstructured":"Following the rules of organic nomenclature, the correct names forN- 2- 3- and 4-formylanilines areN-phenylformamide, 2-aminobenzaldehyde, 3-aminobenzaldehyde, and 4-aminobenzaldehyde, respectively, while the use of 2- 3- and 4-formylphenols is correct. In order to demonstrate that the same group is inserted in the structure of phenol or into aniline,N- 2- 3- and 4-formylaniline will be used throughout this work."},{"key":"ref2\/cit2","doi-asserted-by":"crossref","first-page":"1372","DOI":"10.1016\/j.jct.2007.03.006","volume":"39","author":"Ribeiro da Silva M. D. M. C.","year":"2007","journal-title":"J. Chem. Thermodyn."},{"key":"ref3\/cit3","doi-asserted-by":"crossref","first-page":"10029","DOI":"10.1021\/jp804455u","volume":"112","author":"Bernardes C. E. S.","year":"2008","journal-title":"J. Phys. Chem. A"},{"key":"ref4\/cit4","unstructured":"Bernardes and Minas da Piedade extended also their experimental studies to three other compounds, namely, 2\u2032-hydroxyacetophenone, 2-hydroxybenzamide, and 4-hydroxybenzamide."},{"key":"ref5\/cit5","doi-asserted-by":"crossref","DOI":"10.1201\/9781420007282","volume-title":"Comprehensive Handbook of Chemical Bond Energies","author":"Luo Y. R.","year":"2007"},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"12263","DOI":"10.1021\/jp8065212","volume":"112","author":"Ribeiro da Silva M. A. V.","year":"2008","journal-title":"J. Phys. Chem. A"},{"key":"ref7\/cit7","doi-asserted-by":"crossref","first-page":"517","DOI":"10.1021\/ie50448a022","volume":"39","author":"Stull D. R.","year":"1947","journal-title":"Ind. Eng. Chem."},{"key":"ref8\/cit8","series-title":"NIST Standard Reference Database Number 69","volume-title":"NIST Chemistry WebBook","author":"Linstrom P. J."},{"key":"ref9\/cit9","doi-asserted-by":"crossref","first-page":"4017","DOI":"10.1021\/ja00404a008","volume":"103","author":"Fujio M.","year":"1981","journal-title":"J. Am. Chem. Soc."},{"key":"ref10\/cit10","series-title":"NIST Standard Reference Database Number 69","volume-title":"NIST Chemistry WebBook","author":"Bartmess J. E."},{"key":"ref11\/cit11","doi-asserted-by":"crossref","first-page":"221","DOI":"10.1524\/zpch.1964.42.3_4.221","volume":"42","author":"Foffani A.","year":"1964","journal-title":"Z. Phys. Chem."},{"key":"ref12\/cit12","series-title":"NIST Standard Reference Database Number 69","volume-title":"NIST Chemistry WebBook","author":"Rosenstock H. M."},{"key":"ref13\/cit13","first-page":"602","volume":"3","author":"Zverev V. V.","year":"1992","journal-title":"Izv. Akad. Nauk SSSR, Ser. Khim."},{"key":"ref14\/cit14","series-title":"NIST Standard Reference Database Number 69","volume-title":"NIST Chemistry WebBook","author":"Lias S. G."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","DOI":"10.1007\/978-94-009-3173-2","volume-title":"Handbook of the Thermodynamics of Organic Compounds","author":"Stephenson R. M.","year":"1987"},{"key":"ref16\/cit16","series-title":"NIST Standard Reference Database Number 69","volume-title":"NIST Chemistry WebBook","author":"Chickos J. S."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"860","DOI":"10.1002\/qua.20347","volume":"101","author":"Gomes J. R. B.","year":"2005","journal-title":"Int. J. Quantum Chem."},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"13356","DOI":"10.1021\/jp0519565","volume":"109","author":"Ribeiro da Silva M. A. V.","year":"2005","journal-title":"J. Phys. Chem. B"},{"key":"ref19\/cit19","doi-asserted-by":"crossref","first-page":"1852","DOI":"10.1246\/bcsj.79.1852","volume":"79","author":"Ribeiro da Silva M. A. V.","year":"2006","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1007\/s11224-006-9074-5","volume":"18","author":"Gomes J. R. B.","year":"2007","journal-title":"Struct. Chem."},{"key":"ref21\/cit21","doi-asserted-by":"crossref","first-page":"2052","DOI":"10.1021\/jp0672407","volume":"111","author":"Ribeiro da Silva M. A. V.","year":"2007","journal-title":"J. Phys. Chem. B"},{"key":"ref22\/cit22","doi-asserted-by":"crossref","first-page":"7237","DOI":"10.1021\/jp0729009","volume":"111","author":"Gomes J. R. B.","year":"2007","journal-title":"J. Phys. Chem. A"},{"key":"ref23\/cit23","doi-asserted-by":"crossref","first-page":"7650","DOI":"10.1063\/1.478676","volume":"110","author":"Baboul A. G.","year":"1999","journal-title":"J. Chem. Phys."},{"key":"ref24\/cit24","doi-asserted-by":"crossref","first-page":"618","DOI":"10.1103\/PhysRev.46.618","volume":"46","author":"M\u00f8ller C.","year":"1934","journal-title":"Phys. Rev."},{"key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"7764","DOI":"10.1063\/1.477422","volume":"109","author":"Curtiss L. A.","year":"1998","journal-title":"J. Chem. Phys."},{"key":"ref26\/cit26","volume-title":"Gaussian 03, Revision C.01","author":"Frisch M. J.","year":"2004"},{"key":"ref27\/cit27","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","volume":"98","author":"Becke A. D.","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref28\/cit28","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","volume":"37","author":"Lee C.","year":"1980","journal-title":"Phys. Rev. B"},{"key":"ref29\/cit29","doi-asserted-by":"crossref","first-page":"650","DOI":"10.1063\/1.438955","volume":"72","author":"Krishnan R.","year":"1980","journal-title":"J. Chem. Phys."},{"key":"ref30\/cit30","doi-asserted-by":"crossref","first-page":"13948","DOI":"10.1021\/jp064286r","volume":"110","author":"Gomes J. R. B.","year":"2006","journal-title":"J. Phys. Chem. A"},{"key":"ref31\/cit31","unstructured":"Please notice that the enthalpic difference between results calculated with the atomization or group substitution reactions is constant, both for the three formylphenols and the four formylanilines, since the same reactions were used for the different isomers."},{"key":"ref32\/cit32","series-title":"TRC Data Series","volume-title":"Thermochemical Data and Structures of Organic Compounds","volume":"1","author":"Pedley J. B.","year":"1994"},{"key":"ref33\/cit33","unstructured":"This value is the mean result of the enthalpies of formation calculated with the atomization and group substitution reactions; the associated uncertainty (asun) was calculated asasun= \u221a((\u03a3\u03942)\/(n\u2212 1)) where (\u0394) are the differences between the experimental and calculated enthalpies of formation for 2-formylphenol and 4-formylphenol compounds listed in Table1andnis the number of occurrences, i.e., 6 values of \u0394."},{"key":"ref34\/cit34","doi-asserted-by":"crossref","first-page":"1173","DOI":"10.1021\/ja002455u","volume":"123","author":"Wright J. S.","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref35\/cit35","doi-asserted-by":"crossref","first-page":"407","DOI":"10.3390\/i3040407","volume":"3","author":"Chandra A. K.","year":"2002","journal-title":"Int. J. Mol. Sci."},{"key":"ref36\/cit36","doi-asserted-by":"crossref","first-page":"869","DOI":"10.1021\/jp026707k","volume":"107","author":"Gomes J. R. B.","year":"2003","journal-title":"J. Phys. Chem. A"},{"key":"ref37\/cit37","unstructured":"The exact energy of the hydrogen atom (\u22120.50000 hartree; this value plus thermal corrections is \u22120.49764 hartree) was used to calculate the leftmost result inside parenthesis included in Table2. If the UB3LYP\/6-311+G(2d,2p) energy (\u22120.502156 hartree) is considered, the bond dissociation enthalpies calculated with the B3LYP approach are more positive by 5.7 kJ\/mol (rightmost result in Table2)."},{"key":"ref38\/cit38","doi-asserted-by":"crossref","first-page":"707","DOI":"10.1063\/1.556020","volume":"27","author":"Santos R. M. B.","year":"1998","journal-title":"J. Phys. Chem. Ref. Data"},{"key":"ref39\/cit39","doi-asserted-by":"crossref","first-page":"2647","DOI":"10.1021\/jp047148f","volume":"109","author":"Mulder P.","year":"2005","journal-title":"J. Phys. Chem. A"},{"key":"ref40\/cit40","doi-asserted-by":"crossref","first-page":"3413","DOI":"10.1021\/jo962195s","volume":"62","author":"MacFaul P. A.","year":"1997","journal-title":"J. Org. Chem."},{"key":"ref41\/cit41","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1016\/0009-2614(89)87315-4","volume":"158","author":"Sim\u00f5es J. A. M.","year":"1989","journal-title":"Chem. Phys. Lett."}],"container-title":["The Journal of Physical Chemistry A"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jp8101354","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,5]],"date-time":"2023-04-05T18:55:03Z","timestamp":1680720903000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jp8101354"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,1,26]]},"references-count":41,"journal-issue":{"issue":"8","published-print":{"date-parts":[[2009,2,26]]}},"alternative-id":["10.1021\/jp8101354"],"URL":"https:\/\/doi.org\/10.1021\/jp8101354","relation":{},"ISSN":["1089-5639","1520-5215"],"issn-type":[{"value":"1089-5639","type":"print"},{"value":"1520-5215","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,1,26]]}}}