{"id":"https://openalex.org/W1978665145","doi":"https://doi.org/10.1021/jo050535g","title":"An Enthalpic Scale of Hydrogen-Bond Basicity. 3. Ammonia, Primary, Secondary, and Tertiary Amines","display_name":"An Enthalpic Scale of Hydrogen-Bond Basicity. 3. Ammonia, Primary, Secondary, and Tertiary Amines","publication_year":2005,"publication_date":"2005-09-01","ids":{"openalex":"https://openalex.org/W1978665145","doi":"https://doi.org/10.1021/jo050535g","mag":"1978665145","pmid":"https://pubmed.ncbi.nlm.nih.gov/16277308"},"language":"en","primary_location":{"id":"doi:10.1021/jo050535g","doi":"https://doi.org/10.1021/jo050535g","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo050535g","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5059573239","display_name":"J\u00e9r\u00f4me Graton","orcid":"https://orcid.org/0000-0002-1114-200X","observed_orcids":["https://orcid.org/0000-0002-1114-200X"]},"institutions":[{"id":"https://openalex.org/I1294671590","display_name":"Centre National de la Recherche Scientifique","ror":"https://ror.org/02feahw73","country_code":"FR","type":"government","lineage":["https://openalex.org/I1294671590"]},{"id":"https://openalex.org/I4405260337","display_name":"Universit\u00e9 de Nantes","ror":"https://ror.org/03kjmz544","country_code":"FR","type":"education","lineage":["https://openalex.org/I4405260337","https://openalex.org/I97188460"]},{"id":"https://openalex.org/I97188460","display_name":"Nantes Universit\u00e9","ror":"https://ror.org/03gnr7b55","country_code":"FR","type":"education","lineage":["https://openalex.org/I97188460"]}],"countries":["FR"],"is_corresponding":false,"raw_author_name":"J\u00e9r\u00f4me Graton","raw_affiliation_strings":["Laboratoire de Spectrochimie et Mod\u00e9lisation, EA 1149, FR CNRS 2465, Facult\u00e9 des Sciences et des Techniques, Universit\u00e9 de Nantes, 2, rue de la Houssini\u00e8re, BP 92208, 44322 Nantes, Cedex 3, France"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Laboratoire de Spectrochimie et Mod\u00e9lisation, EA 1149, FR CNRS 2465, Facult\u00e9 des Sciences et des Techniques, Universit\u00e9 de Nantes, 2, rue de la Houssini\u00e8re, BP 92208, 44322 Nantes, Cedex 3, France","institution_ids":["https://openalex.org/I1294671590","https://openalex.org/I4405260337","https://openalex.org/I97188460"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5082046648","display_name":"Michel Berthelot","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I1294671590","display_name":"Centre National de la Recherche Scientifique","ror":"https://ror.org/02feahw73","country_code":"FR","type":"government","lineage":["https://openalex.org/I1294671590"]},{"id":"https://openalex.org/I4405260337","display_name":"Universit\u00e9 de Nantes","ror":"https://ror.org/03kjmz544","country_code":"FR","type":"education","lineage":["https://openalex.org/I4405260337","https://openalex.org/I97188460"]},{"id":"https://openalex.org/I97188460","display_name":"Nantes Universit\u00e9","ror":"https://ror.org/03gnr7b55","country_code":"FR","type":"education","lineage":["https://openalex.org/I97188460"]}],"countries":["FR"],"is_corresponding":false,"raw_author_name":"Michel Berthelot","raw_affiliation_strings":["Laboratoire de Spectrochimie et Mod\u00e9lisation, EA 1149, FR CNRS 2465, Facult\u00e9 des Sciences et des Techniques, Universit\u00e9 de Nantes, 2, rue de la Houssini\u00e8re, BP 92208, 44322 Nantes, Cedex 3, France"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Laboratoire de Spectrochimie et Mod\u00e9lisation, EA 1149, FR CNRS 2465, Facult\u00e9 des Sciences et des Techniques, Universit\u00e9 de Nantes, 2, rue de la Houssini\u00e8re, BP 92208, 44322 Nantes, Cedex 3, France","institution_ids":["https://openalex.org/I1294671590","https://openalex.org/I4405260337","https://openalex.org/I97188460"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5111505992","display_name":"Fran\u00e7ois Besseau","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I1294671590","display_name":"Centre National de la Recherche Scientifique","ror":"https://ror.org/02feahw73","country_code":"FR","type":"government","lineage":["https://openalex.org/I1294671590"]},{"id":"https://openalex.org/I4405260337","display_name":"Universit\u00e9 de Nantes","ror":"https://ror.org/03kjmz544","country_code":"FR","type":"education","lineage":["https://openalex.org/I4405260337","https://openalex.org/I97188460"]},{"id":"https://openalex.org/I97188460","display_name":"Nantes Universit\u00e9","ror":"https://ror.org/03gnr7b55","country_code":"FR","type":"education","lineage":["https://openalex.org/I97188460"]}],"countries":["FR"],"is_corresponding":false,"raw_author_name":"Fran\u00e7ois Besseau","raw_affiliation_strings":["Laboratoire de Spectrochimie et Mod\u00e9lisation, EA 1149, FR CNRS 2465, Facult\u00e9 des Sciences et des Techniques, Universit\u00e9 de Nantes, 2, rue de la Houssini\u00e8re, BP 92208, 44322 Nantes, Cedex 3, France"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Laboratoire de Spectrochimie et Mod\u00e9lisation, EA 1149, FR CNRS 2465, Facult\u00e9 des Sciences et des Techniques, Universit\u00e9 de Nantes, 2, rue de la Houssini\u00e8re, BP 92208, 44322 Nantes, Cedex 3, France","institution_ids":["https://openalex.org/I1294671590","https://openalex.org/I4405260337","https://openalex.org/I97188460"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5111507560","display_name":"Christian Laurence","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I1294671590","display_name":"Centre National de la Recherche Scientifique","ror":"https://ror.org/02feahw73","country_code":"FR","type":"government","lineage":["https://openalex.org/I1294671590"]},{"id":"https://openalex.org/I4405260337","display_name":"Universit\u00e9 de Nantes","ror":"https://ror.org/03kjmz544","country_code":"FR","type":"education","lineage":["https://openalex.org/I4405260337","https://openalex.org/I97188460"]},{"id":"https://openalex.org/I97188460","display_name":"Nantes Universit\u00e9","ror":"https://ror.org/03gnr7b55","country_code":"FR","type":"education","lineage":["https://openalex.org/I97188460"]}],"countries":["FR"],"is_corresponding":false,"raw_author_name":"Christian Laurence","raw_affiliation_strings":["Laboratoire de Spectrochimie et Mod\u00e9lisation, EA 1149, FR CNRS 2465, Facult\u00e9 des Sciences et des Techniques, Universit\u00e9 de Nantes, 2, rue de la Houssini\u00e8re, BP 92208, 44322 Nantes, Cedex 3, France"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Laboratoire de Spectrochimie et Mod\u00e9lisation, EA 1149, FR CNRS 2465, Facult\u00e9 des Sciences et des Techniques, Universit\u00e9 de Nantes, 2, rue de la Houssini\u00e8re, BP 92208, 44322 Nantes, Cedex 3, France","institution_ids":["https://openalex.org/I1294671590","https://openalex.org/I4405260337","https://openalex.org/I97188460"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":3,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.7768,"has_fulltext":false,"cited_by_count":50,"citation_normalized_percentile":{"value":0.81984923,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":87,"max":97},"biblio":{"volume":"70","issue":"20","first_page":"7892","last_page":"7901"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10798","display_name":"Crystallography and molecular interactions","score":0.9185000061988831,"subfield":{"id":"https://openalex.org/subfields/1606","display_name":"Physical and Theoretical Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T10798","display_name":"Crystallography and molecular interactions","score":0.9185000061988831,"subfield":{"id":"https://openalex.org/subfields/1606","display_name":"Physical and Theoretical Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T12191","display_name":"Physical Organic Chemistry and Reaction Kinetics","score":0.0421999990940094,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T12852","display_name":"Chemical Thermodynamics and Molecular Structure","score":0.010999999940395355,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/hydrogen-bond-basicity","display_name":"hydrogen-bond basicity","score":0.9240000247955322},{"id":"https://openalex.org/keywords/aliphatic-amines","display_name":"aliphatic amines","score":0.9110000133514404},{"id":"https://openalex.org/keywords/ammonia","display_name":"ammonia","score":0.7599999904632568},{"id":"https://openalex.org/keywords/primary-secondary-and-tertiary-amines","display_name":"primary, secondary and tertiary amines","score":0.8140000104904175},{"id":"https://openalex.org/keywords/hydrogen-bond-enthalpy","display_name":"hydrogen bond enthalpy","score":0.8859999775886536},{"id":"https://openalex.org/keywords/4-fluorophenol","display_name":"4-fluorophenol","score":0.8690000176429749},{"id":"https://openalex.org/keywords/temperature-dependence","display_name":"temperature dependence","score":0.48100000619888306},{"id":"https://openalex.org/keywords/steric-effects","display_name":"steric effects","score":0.7379999756813049},{"id":"https://openalex.org/keywords/lewis-bases","display_name":"Lewis bases","score":0.8420000076293945},{"id":"https://openalex.org/keywords/infrared-spectroscopy","display_name":"infrared spectroscopy","score":0.46299999952316284}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9184190630912781},{"id":"https://openalex.org/C112887158","wikidata":"https://www.wikidata.org/wiki/Q169324","display_name":"Hydrogen bond","level":3,"score":0.7909886837005615},{"id":"https://openalex.org/C201194858","wikidata":"https://www.wikidata.org/wiki/Q898238","display_name":"Steric effects","level":2,"score":0.7897822260856628},{"id":"https://openalex.org/C3288061","wikidata":"https://www.wikidata.org/wiki/Q161064","display_name":"Enthalpy","level":2,"score":0.7386836409568787},{"id":"https://openalex.org/C122032599","wikidata":"https://www.wikidata.org/wiki/Q2914535","display_name":"Bond energy","level":3,"score":0.5853022933006287},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.5604159235954285},{"id":"https://openalex.org/C2779892579","wikidata":"https://www.wikidata.org/wiki/Q912138","display_name":"Acceptor","level":2,"score":0.5554964542388916},{"id":"https://openalex.org/C512968161","wikidata":"https://www.wikidata.org/wiki/Q556","display_name":"Hydrogen","level":2,"score":0.43258509039878845},{"id":"https://openalex.org/C10710636","wikidata":"https://www.wikidata.org/wiki/Q857809","display_name":"Equilibrium constant","level":2,"score":0.4179471433162689},{"id":"https://openalex.org/C147789679","wikidata":"https://www.wikidata.org/wiki/Q11372","display_name":"Physical chemistry","level":1,"score":0.4172575771808624},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.3539869785308838},{"id":"https://openalex.org/C179104552","wikidata":"https://www.wikidata.org/wiki/Q11165","display_name":"Inorganic chemistry","level":1,"score":0.3409155607223511},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.31746429204940796},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.28955942392349243},{"id":"https://openalex.org/C97355855","wikidata":"https://www.wikidata.org/wiki/Q11473","display_name":"Thermodynamics","level":1,"score":0.2529261112213135},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0},{"id":"https://openalex.org/C26873012","wikidata":"https://www.wikidata.org/wiki/Q214781","display_name":"Condensed matter physics","level":1,"score":0.0}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1021/jo050535g","doi":"https://doi.org/10.1021/jo050535g","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo050535g","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},{"id":"pmid:16277308","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/16277308","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of organic chemistry","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":53,"referenced_works":["https://openalex.org/W1496096284","https://openalex.org/W1497732534","https://openalex.org/W1498235692","https://openalex.org/W1505914198","https://openalex.org/W1937536102","https://openalex.org/W1963802403","https://openalex.org/W1965546181","https://openalex.org/W1976596600","https://openalex.org/W1977114966","https://openalex.org/W1977585488","https://openalex.org/W1977677529","https://openalex.org/W1981141828","https://openalex.org/W1984813188","https://openalex.org/W1984971224","https://openalex.org/W1997458875","https://openalex.org/W1999357396","https://openalex.org/W2000334951","https://openalex.org/W2007899730","https://openalex.org/W2012719897","https://openalex.org/W2013336704","https://openalex.org/W2018055742","https://openalex.org/W2018216217","https://openalex.org/W2032525140","https://openalex.org/W2033362968","https://openalex.org/W2034915881","https://openalex.org/W2034934070","https://openalex.org/W2040127097","https://openalex.org/W2043200019","https://openalex.org/W2043881090","https://openalex.org/W2045322062","https://openalex.org/W2046600214","https://openalex.org/W2046828673","https://openalex.org/W2052528949","https://openalex.org/W2054073238","https://openalex.org/W2057295492","https://openalex.org/W2061926394","https://openalex.org/W2073418783","https://openalex.org/W2077916582","https://openalex.org/W2081595695","https://openalex.org/W2088467437","https://openalex.org/W2088645965","https://openalex.org/W2090360531","https://openalex.org/W2091692227","https://openalex.org/W2093252836","https://openalex.org/W2123847248","https://openalex.org/W2324932860","https://openalex.org/W2330708177","https://openalex.org/W2335058596","https://openalex.org/W2623301821","https://openalex.org/W2623649117","https://openalex.org/W3147068533","https://openalex.org/W4300611374","https://openalex.org/W4388166533"],"related_works":["https://openalex.org/W2046828673","https://openalex.org/W2069814796","https://openalex.org/W1990139587","https://openalex.org/W2005219826","https://openalex.org/W2154445444","https://openalex.org/W2069769758","https://openalex.org/W2248973725","https://openalex.org/W1986607982","https://openalex.org/W2084362488","https://openalex.org/W2020713176"],"abstract_inverted_index":{"A":[0,134],"reliable":[1],"enthalpic":[2,182],"scale":[3,56,183],"of":[4,16,25,30,81,107,122,127,138,148,150,162,192],"hydrogen-bond":[5,26,36,131,181],"acceptor":[6,132],"strength":[7],"(basicity)":[8],"is":[9,73],"built":[10],"for":[11,46,62,68],"aliphatic":[12,154],"amines":[13,128,155],"by":[14,76,88],"means":[15],"a":[17,34,159],"new":[18],"infrared":[19,105],"method,":[20],"from":[21,58,171],"the":[22,77,98,104,108,120,123,139,172,189],"temperature":[23],"variation":[24,72],"equilibrium":[27],"constants.":[28],"Enthalpies":[29],"hydrogen":[31,112,124],"bonding":[32,113],"to":[33,64],"reference":[35],"acceptor,":[37],"4-fluorophenol,":[38],"have":[39,158],"been":[40],"determined":[41],"in":[42,100,119,187],"CCl4":[43],"and/or":[44],"C2Cl4":[45],"ammonia":[47],"and":[48,52,97,116,156],"68":[49],"primary,":[50],"secondary,":[51],"tertiary":[53],"amines.":[54],"The":[55,146,180],"spans":[57],"-23.8":[59],"kJ":[60,66],"mol(-1)":[61,67],"i-Pr2NCH(Et)2":[63],"-39.4":[65],"Et3N.":[69],"This":[70],"large":[71],"mainly":[74,176],"explained":[75],"basicity-enhancing":[78],"electronic":[79,101],"effects":[80],"alkyl":[82],"groups,":[83],"which":[84],"can":[85,184],"be":[86,185],"overcompensated":[87],"dramatic":[89],"basicity-decreasing":[90],"steric":[91],"effects.":[92],"Relationships":[93],"between":[94,153],"DeltaH":[95],"degrees":[96],"change":[99],"energy":[102],"or":[103],"shift":[106],"OH":[109],"stretching":[110],"upon":[111],"are":[114,175],"studied":[115],"found":[117],"useful":[118,186],"prediction":[121],"bond":[125],"enthalpies":[126],"with":[129],"several":[130],"sites.":[133],"careful":[135],"statistical":[136],"analysis":[137],"enthalpy-entropy":[140],"relationship":[141],"shows":[142],"an":[143],"isoentropic":[144,173],"tendency.":[145],"entropies":[147],"65%":[149],"hydrogen-bonding":[151],"reactions":[152],"4-fluorophenol":[157],"mean":[160],"value":[161],"-55.1":[163],"+/-":[164],"4.2":[165],"J":[166],"K(-1)":[167],"mol(-1).":[168],"Amines":[169],"excluded":[170],"set":[174],"severely":[177],"hindered":[178],"ones.":[179],"measuring":[188],"electrostatic":[190],"character":[191],"Lewis":[193],"bases.":[194]},"counts_by_year":[{"year":2026,"cited_by_count":2},{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":2},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":4},{"year":2021,"cited_by_count":1},{"year":2020,"cited_by_count":2},{"year":2019,"cited_by_count":2},{"year":2018,"cited_by_count":2},{"year":2017,"cited_by_count":1},{"year":2016,"cited_by_count":3},{"year":2015,"cited_by_count":1},{"year":2014,"cited_by_count":2},{"year":2013,"cited_by_count":2},{"year":2012,"cited_by_count":3}],"updated_date":"2026-11-12T12:28:57.059296","created_date":"2016-06-24T00:00:00"}
