{"id":"https://openalex.org/W7172391885","doi":"https://doi.org/10.1021/acs.cgd.6c00310","title":"Phenyl and Benzyl Azido Carboxylic Acids: Exploring the Organic Azide Alongside the Carboxylic Acid\u2013Pyridine Supramolecular Synthon","display_name":"Phenyl and Benzyl Azido Carboxylic Acids: Exploring the Organic Azide Alongside the Carboxylic Acid\u2013Pyridine Supramolecular Synthon","publication_year":2026,"publication_date":"2026-07-28","ids":{"openalex":"https://openalex.org/W7172391885","doi":"https://doi.org/10.1021/acs.cgd.6c00310"},"language":"en","primary_location":{"id":"doi:10.1021/acs.cgd.6c00310","doi":"https://doi.org/10.1021/acs.cgd.6c00310","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.cgd.6c00310","pdf_url":null,"source":{"id":"https://openalex.org/S16561315","display_name":"Crystal Growth & Design","issn_l":"1528-7483","issn":["1528-7483","1528-7505"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-c","jufo-2","norway-2","poland-100","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":"Crystal Growth &amp; Design","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref"],"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/A5051627452","display_name":"Daniel A. Decato","orcid":"https://orcid.org/0009-0008-0678-4455","observed_orcids":["https://orcid.org/0009-0008-0678-4455"]},"institutions":[{"id":"https://openalex.org/I6750721","display_name":"University of Montana","ror":"https://ror.org/0078xmk34","country_code":"US","type":"education","lineage":["https://openalex.org/I6750721"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Daniel A. Decato","raw_affiliation_strings":["University of Montana , , 32 Campus Drive , , ,"],"raw_orcid":"https://orcid.org/0009-0008-0678-4455","affiliations":[{"raw_affiliation_string":"University of Montana , , 32 Campus Drive , , ,","institution_ids":["https://openalex.org/I6750721"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5040930268","display_name":"Stefan Peintner","orcid":"https://orcid.org/0000-0001-9882-2018","observed_orcids":["https://orcid.org/0000-0001-9882-2018"]},"institutions":[{"id":"https://openalex.org/I6750721","display_name":"University of Montana","ror":"https://ror.org/0078xmk34","country_code":"US","type":"education","lineage":["https://openalex.org/I6750721"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Stefan Peintner","raw_affiliation_strings":["University of Montana , , 32 Campus Drive , , ,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"University of Montana , , 32 Campus Drive , , ,","institution_ids":["https://openalex.org/I6750721"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5039068825","display_name":"Michael Jahnke","orcid":"https://orcid.org/0009-0002-7967-9409","observed_orcids":["https://orcid.org/0009-0002-7967-9409"]},"institutions":[{"id":"https://openalex.org/I6750721","display_name":"University of Montana","ror":"https://ror.org/0078xmk34","country_code":"US","type":"education","lineage":["https://openalex.org/I6750721"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Michael Jahnke","raw_affiliation_strings":["University of Montana , , 32 Campus Drive , , ,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"University of Montana , , 32 Campus Drive , , ,","institution_ids":["https://openalex.org/I6750721"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5030055806","display_name":"Orion B. Berryman","orcid":"https://orcid.org/0000-0002-0324-484X","observed_orcids":["https://orcid.org/0000-0002-0324-484X"]},"institutions":[{"id":"https://openalex.org/I6750721","display_name":"University of Montana","ror":"https://ror.org/0078xmk34","country_code":"US","type":"education","lineage":["https://openalex.org/I6750721"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Orion B. Berryman","raw_affiliation_strings":["University of Montana , , 32 Campus Drive , , ,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"University of Montana , , 32 Campus Drive , , ,","institution_ids":["https://openalex.org/I6750721"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5051627452"],"corresponding_institution_ids":["https://openalex.org/I6750721"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":0.0,"has_fulltext":false,"cited_by_count":0,"citation_normalized_percentile":{"value":0.48828996,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":null,"biblio":{"volume":"26","issue":"16","first_page":"6377","last_page":"6390"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10798","display_name":"Crystallography and molecular interactions","score":0.9976000189781189,"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":0.9976000189781189,"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/T10578","display_name":"Supramolecular Chemistry and Complexes","score":0.000699999975040555,"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/T11419","display_name":"Supramolecular Self-Assembly in Materials","score":0.0005000000237487257,"subfield":{"id":"https://openalex.org/subfields/2502","display_name":"Biomaterials"},"field":{"id":"https://openalex.org/fields/25","display_name":"Materials Science"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/azide-compounds","display_name":"azido compounds","score":0.8379999995231628},{"id":"https://openalex.org/keywords/crystal-engineering","display_name":"crystal engineering","score":0.9150000214576721},{"id":"https://openalex.org/keywords/crystal-packing","display_name":"crystal packing","score":0.7599999904632568},{"id":"https://openalex.org/keywords/hydrogen-bonding","display_name":"hydrogen bonding","score":0.8339999914169312},{"id":"https://openalex.org/keywords/halogen-bonding","display_name":"halogen bonding","score":0.7390000224113464}],"concepts":[{"id":"https://openalex.org/C40869318","wikidata":"https://www.wikidata.org/wiki/Q899050","display_name":"Synthon","level":2,"score":0.9815000295639038},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8241000175476074},{"id":"https://openalex.org/C5716244","wikidata":"https://www.wikidata.org/wiki/Q5191408","display_name":"Crystal engineering","level":4,"score":0.8220999836921692},{"id":"https://openalex.org/C93275456","wikidata":"https://www.wikidata.org/wiki/Q756449","display_name":"Supramolecular chemistry","level":3,"score":0.794700026512146},{"id":"https://openalex.org/C2780997848","wikidata":"https://www.wikidata.org/wiki/Q407627","display_name":"Azide","level":2,"score":0.7041000127792358},{"id":"https://openalex.org/C2779485729","wikidata":"https://www.wikidata.org/wiki/Q210385","display_name":"Pyridine","level":2,"score":0.6428999900817871},{"id":"https://openalex.org/C112887158","wikidata":"https://www.wikidata.org/wiki/Q169324","display_name":"Hydrogen bond","level":3,"score":0.5821999907493591},{"id":"https://openalex.org/C23029723","wikidata":"https://www.wikidata.org/wiki/Q1193318","display_name":"Halogen bond","level":4,"score":0.5759999752044678},{"id":"https://openalex.org/C178516000","wikidata":"https://www.wikidata.org/wiki/Q3023362","display_name":"Denticity","level":3,"score":0.44040000438690186},{"id":"https://openalex.org/C115624301","wikidata":"https://www.wikidata.org/wiki/Q895901","display_name":"Crystal structure","level":2,"score":0.42080000042915344},{"id":"https://openalex.org/C2779074116","wikidata":"https://www.wikidata.org/wiki/Q134856","display_name":"Carboxylic acid","level":2,"score":0.38929998874664307},{"id":"https://openalex.org/C46062151","wikidata":"https://www.wikidata.org/wiki/Q19605","display_name":"Halogen","level":3,"score":0.3792000114917755},{"id":"https://openalex.org/C2779892579","wikidata":"https://www.wikidata.org/wiki/Q912138","display_name":"Acceptor","level":2,"score":0.3443000018596649},{"id":"https://openalex.org/C188027245","wikidata":"https://www.wikidata.org/wiki/Q750446","display_name":"Polymer chemistry","level":1,"score":0.33160001039505005},{"id":"https://openalex.org/C137277065","wikidata":"https://www.wikidata.org/wiki/Q2915446","display_name":"Non-covalent interactions","level":4,"score":0.33000001311302185},{"id":"https://openalex.org/C2781285689","wikidata":"https://www.wikidata.org/wiki/Q21921428","display_name":"Crystal (programming language)","level":2,"score":0.329800009727478},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.31940001249313354},{"id":"https://openalex.org/C192406513","wikidata":"https://www.wikidata.org/wiki/Q2427921","display_name":"Supramolecular assembly","level":4,"score":0.3181999921798706},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.3176000118255615},{"id":"https://openalex.org/C535685238","wikidata":"https://www.wikidata.org/wiki/Q1153832","display_name":"Organic synthesis","level":3,"score":0.31349998712539673},{"id":"https://openalex.org/C2781076698","wikidata":"https://www.wikidata.org/wiki/Q718074","display_name":"Aryl","level":3,"score":0.2775999903678894},{"id":"https://openalex.org/C68913812","wikidata":"https://www.wikidata.org/wiki/Q238156","display_name":"Coordination complex","level":3,"score":0.27549999952316284},{"id":"https://openalex.org/C18705241","wikidata":"https://www.wikidata.org/wiki/Q1128023","display_name":"Conformational isomerism","level":3,"score":0.273499995470047},{"id":"https://openalex.org/C192386470","wikidata":"https://www.wikidata.org/wiki/Q210390","display_name":"Aromaticity","level":3,"score":0.26159998774528503},{"id":"https://openalex.org/C75473681","wikidata":"https://www.wikidata.org/wiki/Q188651","display_name":"Photochemistry","level":1,"score":0.2596000134944916},{"id":"https://openalex.org/C2779664164","wikidata":"https://www.wikidata.org/wiki/Q898648","display_name":"Cycloaddition","level":3,"score":0.25619998574256897}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1021/acs.cgd.6c00310","doi":"https://doi.org/10.1021/acs.cgd.6c00310","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.cgd.6c00310","pdf_url":null,"source":{"id":"https://openalex.org/S16561315","display_name":"Crystal Growth & Design","issn_l":"1528-7483","issn":["1528-7483","1528-7505"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-c","jufo-2","norway-2","poland-100","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":"Crystal Growth &amp; Design","raw_type":"journal-article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G1310521215","display_name":null,"funder_award_id":"1337908","funder_id":"https://openalex.org/F4320337393","funder_display_name":"Division of Chemistry"},{"id":"https://openalex.org/G3214785821","display_name":null,"funder_award_id":"202119871","funder_id":"https://openalex.org/F4320306203","funder_display_name":"M.J. Murdock Charitable Trust"},{"id":"https://openalex.org/G9000875314","display_name":"Biomolecular Structure and Dynamics","funder_award_id":"P30GM140963","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320306203","display_name":"M.J. Murdock Charitable Trust","ror":"https://ror.org/02hxgd925"},{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"},{"id":"https://openalex.org/F4320337393","display_name":"Division of Chemistry","ror":"https://ror.org/01ar8dr59"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":34,"referenced_works":["https://openalex.org/W1964658576","https://openalex.org/W1969360633","https://openalex.org/W1978633893","https://openalex.org/W1980996453","https://openalex.org/W1990437495","https://openalex.org/W1998920258","https://openalex.org/W1999041499","https://openalex.org/W2017702218","https://openalex.org/W2020087097","https://openalex.org/W2021200484","https://openalex.org/W2034004639","https://openalex.org/W2039614178","https://openalex.org/W2059205366","https://openalex.org/W2101547779","https://openalex.org/W2132454074","https://openalex.org/W2135824076","https://openalex.org/W2161988924","https://openalex.org/W2319902168","https://openalex.org/W2532612623","https://openalex.org/W2619390033","https://openalex.org/W2749170036","https://openalex.org/W2980313702","https://openalex.org/W3092876455","https://openalex.org/W3173609270","https://openalex.org/W3193856292","https://openalex.org/W3193945445","https://openalex.org/W3215124921","https://openalex.org/W4210506302","https://openalex.org/W4220722176","https://openalex.org/W4224303788","https://openalex.org/W4246712716","https://openalex.org/W4388484012","https://openalex.org/W4391126767","https://openalex.org/W4395110645"],"related_works":["https://openalex.org/W4402652579","https://openalex.org/W2059910175","https://openalex.org/W2161579703","https://openalex.org/W2049011001","https://openalex.org/W2022191496","https://openalex.org/W3193945445","https://openalex.org/W2179534366","https://openalex.org/W2068270420","https://openalex.org/W4400352143","https://openalex.org/W2014781938"],"abstract_inverted_index":{"Abstract":[0],"Organic":[1],"azides":[2,177],"are":[3,178],"widely":[4],"used":[5],"in":[6,14,166,189],"synthetic":[7],"organic":[8,33],"chemistry":[9],"but":[10],"remain":[11],"comparatively":[12],"rare":[13],"crystal":[15,43,139,191],"engineering.":[16],"This":[17],"work":[18],"leverages":[19],"the":[20,37,56,63,69,83,100,108,138,150,185,195,209],"carboxylic":[21,50],"acid\u2013pyridine":[22],"(CA\u2013Py)":[23],"supramolecular":[24,197],"synthon":[25,58,198],"to":[26,82,91,134,161],"systematically":[27],"evaluate":[28],"if":[29],"and":[30,48,59,102,124,153,175],"how":[31],"an":[32,144,213],"azide":[34,84,115,160],"may":[35,203],"influence":[36],"packing.":[38],"We":[39],"present":[40],"31":[41],"multicomponent":[42],"structures":[44,53],"pairing":[45],"substituted":[46],"pyridines":[47],"azido":[49,154],"acids.":[51],"All":[52],"reported":[54],"retain":[55],"CA\u2013Py":[57,70,196],"display":[60],"many":[61],"of":[62,75,104],"common":[64],"secondary":[65],"interactions":[66,113,129],"associated":[67],"with":[68],"synthon.":[71],"A":[72],"limited":[73],"number":[74,101],"weak,":[76],"monodentate":[77],"N\u2013H":[78],"hydrogen":[79],"bonds":[80,148],"(HBs)":[81],"were":[85,116],"observed":[86],"either":[87],"by":[88,97,137],"forced":[89],"proximity":[90],"a":[92,163,205],"better":[93],"HB":[94],"acceptor":[95],"or":[96],"increasing":[98],"both":[99],"positioning":[103],"hydrogen-bond":[105],"donors":[106],"on":[107,184],"pyridine":[109,210],"coformer.":[110],"Additional":[111],"noncovalent":[112],"involving":[114],"also":[117],"considered":[118],"(such":[119],"as":[120],"C\u2013H":[121],"HBs,":[122,201],"azide\u2013azide,":[123],"azide\u2013oxygen":[125],"interactions),":[126],"yet":[127,202],"these":[128],"offered":[130],"no":[131],"systematic":[132],"trends":[133],"be":[135],"leveraged":[136],"engineer.":[140],"In":[141],"contrast,":[142],"evaluating":[143],"iodopyridine":[145],"showed":[146],"halogen":[147,216],"between":[149],"iodine":[151,214],"donor":[152],"nitrogen":[155],"atoms,":[156],"demonstrating":[157],"potential":[158],"for":[159,215],"play":[162,204],"larger":[164,206],"role":[165,207],"directing":[167],"crystalline":[168,187],"assembly.":[169],"Overall,":[170],"we":[171],"conclude":[172],"that":[173],"phenyl":[174],"benzyl":[176],"seemingly":[179],"bystanders,":[180],"having":[181],"minimal":[182],"impact":[183],"final":[186],"assembly":[188],"smaller":[190],"engineering":[192],"systems":[193],"leveraging":[194],"alongside":[199],"other":[200],"when":[208],"conformer":[211],"contains":[212],"bonding.":[217]},"counts_by_year":[],"updated_date":"2026-10-30T12:39:25.321706","created_date":"2026-08-05T00:00:00"}
