{"id":{"repo_id":"bologna","oai_identifier":"oai:amsdottorato.cib.unibo.it:1044"},"canonical_url":"https://search.dev.ndltd.org/etd/bologna/oai:amsdottorato.cib.unibo.it:1044","repository":{"repo_id":"bologna","name":"Università di Bologna","base_url":"https://amsdottorato.unibo.it/cgi/oai2"},"display":{"title":"Sintesi e coordinazione di leganti Ciclopentadienilici O-Multifunzionalizzati","abstract":"The introduction of hydroxyl groups into ligands is able to transfer high hydrophilic features to the related metal systems. The atom-economy synthetic procedure adopted which consists in the one-step Cyclopentene-oxide ring opening, quantitatitatively affords stereoselective formation of the multi-hydroxyl rac-1,2,4- C5H2[CH(CH2)3CHOH]3 Cpººº ligand1. Rh complexation of Cpººº gives rise to a novel class of water-soluble complexes (L,L)RhCpººº (LL=NBD 1, COD 2, CH2CH2 3, CO 4) (Scheme 1) characterized by their spectroscopic features (ESI-MS, IR, 2D NMR, n.O.e.). The X-ray diffraction studies of 1a reveal the occurrence of one couple of enantiomeric pairs in the crystal structure, whilst the crystal packing shows an interesting self-organization in chains of dimeric units of 1a, promoted by strong intermolecular hydroxyl H-bonding. This effect has been exploited by performing VT NMR experiments in different solvents (CDCl3, Py, DMSO). Unpredictably, in the absence of chiral tag, 1 exhibits solvent-dependent chiroptical properties (CD, αD^ 25), which are correlated to UV transitions and DFT calculations. The intra/inter molecular H-binding is crucial in driving the equilibrium between the observed atropisomers 1a and 1b, by varying the planar chirality on the two π-complexes.","abstract_html":"The introduction of hydroxyl groups into ligands is able to transfer high hydrophilic features to the related metal systems. The atom-economy synthetic procedure adopted which consists in the one-step Cyclopentene-oxide ring opening, quantitatitatively affords stereoselective formation of the multi-hydroxyl rac-1,2,4- C5H2[CH(CH2)3CHOH]3 Cpººº ligand1. Rh complexation of Cpººº gives rise to a novel class of water-soluble complexes (L,L)RhCpººº (LL=NBD 1, COD 2, CH2CH2 3, CO 4) (Scheme 1) characterized by their spectroscopic features (ESI-MS, IR, 2D NMR, n.O.e.). The X-ray diffraction studies of 1a reveal the occurrence of one couple of enantiomeric pairs in the crystal structure, whilst the crystal packing shows an interesting self-organization in chains of dimeric units of 1a, promoted by strong intermolecular hydroxyl H-bonding. This effect has been exploited by performing VT NMR experiments in different solvents (CDCl3, Py, DMSO). Unpredictably, in the absence of chiral tag, 1 exhibits solvent-dependent chiroptical properties (CD, αD^ 25), which are correlated to UV transitions and DFT calculations. The intra/inter molecular H-binding is crucial in driving the equilibrium between the observed atropisomers 1a and 1b, by varying the planar chirality on the two π-complexes.","abstract_has_math":false,"creators":["Natanti, Paolo <1979>"],"institution":"Alma Mater Studiorum - Università di Bologna","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":["Bordoni, Silvia"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2008,"date_issued":"2008-04-15","date_published":"2008-04-15","updated_at":"2026-07-24T01:12:05Z","subjects":["CHIM/03 Chimica generale e inorganica"],"languages":["it"],"rights":["info:eu-repo/semantics/openAccess"],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["urn:nbn:it:unibo-1012"],"render_values":[{"text":"urn:nbn:it:unibo-1012","href":null,"code":true}]}]},"links":{"outbound_url":"https://doi.org/10.6092/unibo/amsdottorato/1044.","outbound_label":"DOI","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Bordoni, Silvia"]},{"key":"dc:creator","label":"Author","values":["Natanti, Paolo <1979>"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2008-04-15"]},{"key":"dc:publisher","label":"Institution","values":["Alma Mater Studiorum - Università di Bologna"]},{"key":"dc:relation","label":"Dc Relation","values":["https://amsdottorato.unibo.it/id/eprint/1044/"]},{"key":"dc:type","label":"Dc Type","values":["Doctoral Thesis","PeerReviewed"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["CHIM/03 Chimica generale e inorganica"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["it"]},{"key":"dc:rights","label":"Dc Rights","values":["info:eu-repo/semantics/openAccess"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://amsdottorato.unibo.it/id/eprint/1044/1/Tesi_Natanti_Paolo.pdf","urn:nbn:it:unibo-1012","Natanti, Paolo (2008) Sintesi e coordinazione di leganti Ciclopentadienilici O-Multifunzionalizzati, [Dissertation thesis], Alma Mater Studiorum Università di Bologna. Dottorato di ricerca in Scienze chimiche <https://amsdottorato.unibo.it/view/dottorati/DOT298/>, 20 Ciclo. DOI 10.6092/unibo/amsdottorato/1044."]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["The introduction of hydroxyl groups into ligands is able to transfer high hydrophilic features to the related metal systems. The atom-economy synthetic procedure adopted which consists in the one-step Cyclopentene-oxide ring opening, quantitatitatively affords stereoselective formation of the multi-hydroxyl rac-1,2,4- C5H2[CH(CH2)3CHOH]3 Cpººº ligand1. Rh complexation of Cpººº gives rise to a novel class of water-soluble complexes (L,L)RhCpººº (LL=NBD 1, COD 2, CH2CH2 3, CO 4) (Scheme 1) characterized by their spectroscopic features (ESI-MS, IR, 2D NMR, n.O.e.). The X-ray diffraction studies of 1a reveal the occurrence of one couple of enantiomeric pairs in the crystal structure, whilst the crystal packing shows an interesting self-organization in chains of dimeric units of 1a, promoted by strong intermolecular hydroxyl H-bonding. This effect has been exploited by performing VT NMR experiments in different solvents (CDCl3, Py, DMSO). Unpredictably, in the absence of chiral tag, 1 exhibits solvent-dependent chiroptical properties (CD, αD^ 25), which are correlated to UV transitions and DFT calculations. The intra/inter molecular H-binding is crucial in driving the equilibrium between the observed atropisomers 1a and 1b, by varying the planar chirality on the two π-complexes."]},{"key":"dc:format","label":"Dc Format","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Sintesi e coordinazione di leganti Ciclopentadienilici O-Multifunzionalizzati"]}]}],"canonical_facts":{"dc:contributor":["Bordoni, Silvia"],"dc:creator":["Natanti, Paolo <1979>"],"dc:date":["2008-04-15"],"dc:description":["The introduction of hydroxyl groups into ligands is able to transfer high hydrophilic features to the related metal systems. The atom-economy synthetic procedure adopted which consists in the one-step Cyclopentene-oxide ring opening, quantitatitatively affords stereoselective formation of the multi-hydroxyl rac-1,2,4- C5H2[CH(CH2)3CHOH]3 Cpººº ligand1. Rh complexation of Cpººº gives rise to a novel class of water-soluble complexes (L,L)RhCpººº (LL=NBD 1, COD 2, CH2CH2 3, CO 4) (Scheme 1) characterized by their spectroscopic features (ESI-MS, IR, 2D NMR, n.O.e.). The X-ray diffraction studies of 1a reveal the occurrence of one couple of enantiomeric pairs in the crystal structure, whilst the crystal packing shows an interesting self-organization in chains of dimeric units of 1a, promoted by strong intermolecular hydroxyl H-bonding. This effect has been exploited by performing VT NMR experiments in different solvents (CDCl3, Py, DMSO). Unpredictably, in the absence of chiral tag, 1 exhibits solvent-dependent chiroptical properties (CD, αD^ 25), which are correlated to UV transitions and DFT calculations. The intra/inter molecular H-binding is crucial in driving the equilibrium between the observed atropisomers 1a and 1b, by varying the planar chirality on the two π-complexes."],"dc:format":["application/pdf"],"dc:identifier":["https://amsdottorato.unibo.it/id/eprint/1044/1/Tesi_Natanti_Paolo.pdf","urn:nbn:it:unibo-1012","Natanti, Paolo (2008) Sintesi e coordinazione di leganti Ciclopentadienilici O-Multifunzionalizzati, [Dissertation thesis], Alma Mater Studiorum Università di Bologna. Dottorato di ricerca in Scienze chimiche <https://amsdottorato.unibo.it/view/dottorati/DOT298/>, 20 Ciclo. DOI 10.6092/unibo/amsdottorato/1044."],"dc:language":["it"],"dc:publisher":["Alma Mater Studiorum - Università di Bologna"],"dc:relation":["https://amsdottorato.unibo.it/id/eprint/1044/"],"dc:rights":["info:eu-repo/semantics/openAccess"],"dc:subject":["CHIM/03 Chimica generale e inorganica"],"dc:title":["Sintesi e coordinazione di leganti Ciclopentadienilici O-Multifunzionalizzati"],"dc:type":["Doctoral Thesis","PeerReviewed"]},"updated_at":"2026-07-24T01:12:05Z"}