TY - JOUR AU - Bánhegyi, Dorottya Fruzsina AU - Madarász, János AU - Fogassy, Elemér AU - Pálovics, Emese Csilla AU - Pokol, György TI - Crystalline Forms of 4,4'-Methylenediantipyrine: Crystallographic Unit Cell for the Anhydrous Form, from Laboratory Powder XRD Pattern by DASH Program Package JF - PERIODICA POLYTECHNICA-CHEMICAL ENGINEERING J2 - PERIOD POLYTECH CHEM ENG VL - 67 PY - 2023 IS - 4 SP - 557 EP - 564 PG - 8 SN - 0324-5853 DO - 10.3311/PPch.22950 UR - https://m2.mtmt.hu/api/publication/34204776 ID - 34204776 N1 - Funding Agency and Grant Number: National Research, Development and Innovation Office-NKFIH through OTKA [124180, FK138475, 146218] Funding text: E.F. and E.P. are grateful for the past and future support of the National Research, Development and Innovation Office-NKFIH through OTKA grant Nos. 124180 and FK138475 and 146218, respectively. The authors are also grateful to Mr. David Susko for his substantial help in the preparative work. AB - Crystalline unit cell structure of anhydrous title compound, diantipyrinylmethane (CAS Registry No. 1251-85-0), a substance usually obtained as a by-product in Mannich type reactions of antipyrine, has been modelled by the help of powder X-ray diffraction, applying the DASH software package and crystal coordinates coming from former single crystal X-ray structure determinations (CSD codes FADDIY and FADDIY01) of its monohydrate. The unit cell of the anhydrate compound belongs to the monoclinic space group P21/a, with unit cell parameters of a = 14.604, b = 9.858, c = 14.509 Å, β = 95.56 °, V = 2078.9 Å3, Z = 4, Z ' = 1. Comparisons of FT-IR spectrum and thermal behavior of the anhydrous and monohydrated forms confirm differences in degree of hydration and solid state structure, while those of 1H- and 13C NMR-spectra show their molecular identity. LA - English DB - MTMT ER - TY - JOUR AU - Varga, Bence AU - Buna, Levente AU - Vincze, Daniella AU - Holczbauer, Tamás AU - Mátravölgyi, Béla AU - Fogassy, Elemér AU - Keglevich, György AU - Bagi, Péter TI - Enantioseparation of P-Stereogenic 1-Adamantyl Arylthiophosphonates and Their Stereospecific Transformation to 1-Adamantyl Aryl-H-phosphinates JF - MOLECULES J2 - MOLECULES VL - 28 PY - 2023 IS - 4 PG - 14 SN - 1420-3049 DO - 10.3390/molecules28041584 UR - https://m2.mtmt.hu/api/publication/33635097 ID - 33635097 N1 - Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3, Budapest, H-1111, Hungary Center for Structural Science, Chemical Crystallography Research Laboratory and Institute for Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2, Budapest, H-1519, Hungary Export Date: 20 March 2023 CODEN: MOLEF Correspondence Address: Varga, B.; Department of Organic Chemistry and Technology, Műegyetem rkp. 3, Hungary; email: bencevarga@edu.bme.hu Correspondence Address: Bagi, P.; Department of Organic Chemistry and Technology, Műegyetem rkp. 3, Hungary; email: bagi.peter@vbk.bme.hu AB - A focused library of 1-adamantyl arylthiophosphonates was prepared in racemic form. An enantioseparation method was developed for P-stereogenic thiophosphonates using (S)-1-phenylethylamine as the resolving agent. Under optimized conditions, three out of the five arylthiophosphonates were prepared in enantiopure form (ee > 99%). The subsequent desulfurization of optically active arylthiophosphonates gave the corresponding H-phosphinates without significant erosion of enantiomeric purity (ee = 95–98%). Hence, this reaction sequence can be considered an alternative method for the preparation of 1-adamantyl aryl-H-phopshinates. The absolute configuration of the (S)-1-adamantyl phenylphosphonothioic acid was assigned using single-crystal XRD and it allowed the confirmation that the removal of the P = S group proceeds with retention of configuration. The organocatalytic applicability of (S)-1-adamantyl phenylphosphonothioic acid was also evaluated as a P-stereogenic Brønsted acid. LA - English DB - MTMT ER - TY - JOUR AU - Pálovics, Emese Csilla AU - Madarász, János AU - Pokol, György AU - Fogassy, Elemér AU - Bánhegyi, Dorottya Fruzsina TI - Economic Separations of Organic Acidic or Basic Enantiomeric Mixtures—A Protocol Suggestion JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 24 PY - 2023 IS - 1 PG - 23 SN - 1661-6596 DO - 10.3390/ijms24010846 UR - https://m2.mtmt.hu/api/publication/33543852 ID - 33543852 N1 - Funding Agency and Grant Number: National Research, Development and Innovation Office-NKFIH [FK138475] Funding text: This research was funded by the National Research, Development and Innovation Office-NKFIH, Grant/Award Number: FK138475. AB - In this review, we aim to present new concepts for the revisited separation of enantiomers from racemic compounds and a protocol worth to be followed in designing the preparation of pure enantiomers. We have taken into account not only the influence of the properties (eutectic composition) and characteristics of the reactants (racemic compound, resolving agent), but also the behavior of the resulting diastereomers and the different conditions (e.g., crystallization time, solvents used, solvate-forming compounds, achiral additives, etc.). The examples discussed are resolutions developed by our research team, through which we will try to illustrate the impact of all these considerations, presenting the methodological investigations interpreting recent discoveries and observations. Some special solid-state analytical and structural investigations assisting us in the elucidation and invention design of the resolution processes of some active pharmaceutical ingredients, such as Tetramisole, tofisopam, and Amlodipine, are also shown. LA - English DB - MTMT ER - TY - JOUR AU - Bánhegyi, Dorottya Fruzsina AU - Fogassy, Elemér AU - Madarász, János AU - Pálovics, Emese Csilla TI - Optical Resolution of Two Pharmaceutical Bases with Various Uses of Tartaric Acid Derivatives and Their Sodium Salts: Racemic Ephedrine and Chloramphenicol Base JF - MOLECULES J2 - MOLECULES VL - 27 PY - 2022 IS - 10 SN - 1420-3049 DO - 10.3390/molecules27103134 UR - https://m2.mtmt.hu/api/publication/32827003 ID - 32827003 N1 - Funding Agency and Grant Number: National Research, Development and Innovation Office-NKFIH through OTKA [124180] Funding text: This work was supported by the National Research, Development and Innovation Office-NKFIH through OTKA grant 124180. LA - English DB - MTMT ER - TY - JOUR AU - Varga, Bence AU - Vincze, Daniella AU - Pető, Hajnalka AU - Buna, Levente AU - Pauló, János AU - Holczbauer, Tamás AU - Mátravölgyi, Béla AU - Hegedűs, László AU - Fogassy, Elemér AU - Keglevich, György AU - Bagi, Péter TI - Resolution of aryl-H-phosphinates applied in the synthesis of P-stereogenic compounds including a Brønsted acid NMR solvating agent JF - ORGANIC CHEMISTRY FRONTIERS J2 - ORG CHEM FRONT VL - 9 PY - 2022 IS - 10 SP - 2797 EP - 2807 PG - 11 SN - 2052-4110 DO - 10.1039/D2QO00241H UR - https://m2.mtmt.hu/api/publication/32776910 ID - 32776910 N1 - Funding Agency and Grant Number: New National Excellence Program of the Ministry of Human Capacities [UNKP-21-3-II-BME-299]; National Research, Development and Innovation Office-NKFIHNational Research, Development & Innovation Office (NRDIO) - Hungary; OTKAOrszagos Tudomanyos Kutatasi Alapprogramok (OTKA) [PD 128504] Funding text: B. V. acknowledges the financial support from the New National Excellence Program of the Ministry of Human Capacities (UNKP-21-3-II-BME-299). T.H. is grateful for the support from the National Research, Development and Innovation Office-NKFIH (Grant No. OTKA PD 128504). LA - English DB - MTMT ER - TY - JOUR AU - Fogassy, Elemér TI - Néhány gondolat egy klasszikus kapcsán JF - MAGYAR KÉMIKUSOK LAPJA J2 - MAGY KEM LAP VL - 76 PY - 2021 IS - 7-8 SP - 229 EP - 229 PG - 1 SN - 0025-0163 UR - https://m2.mtmt.hu/api/publication/32585255 ID - 32585255 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Varga, Bence AU - Szemesi, Péter AU - Nagy, Petra AU - Herbay, Réka AU - Holczbauer, Tamás AU - Fogassy, Elemér AU - Keglevich, György AU - Bagi, Péter TI - Enantioseparation of P-Stereogenic Secondary Phosphine Oxides and Their Stereospecific Transformation to Various Tertiary Phosphine Oxides and a Thiophosphinate JF - JOURNAL OF ORGANIC CHEMISTRY J2 - J ORG CHEM VL - 86 PY - 2021 IS - 21 SP - 14493 EP - 14507 PG - 15 SN - 0022-3263 DO - 10.1021/acs.joc.1c01364 UR - https://m2.mtmt.hu/api/publication/32487501 ID - 32487501 N1 - Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Müegyetem rkp. 3, Budapest, H-1111, Hungary Gedeon Richter Plc., Budapest, H-1475, Hungary Center for Structural Science, Chemical Crystallography Research Laboratory, Institute for Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2, Budapest, H-1519, Hungary Export Date: 1 December 2021 CODEN: JOCEA Correspondence Address: Bagi, P.; Department of Organic Chemistry and Technology, Müegyetem rkp. 3, Hungary; email: bagi.peter@vbk.bme.hu LA - English DB - MTMT ER - TY - JOUR AU - Bánhegyi, Dorottya Fruzsina AU - Fogassy, Elemér AU - Pálovics, Emese Csilla TI - Possibilities of Exploiting Kinetic Control in the Continuous Fractional Crystallization of Diastereomeric Mixtures JF - SYMMETRY (BASEL) J2 - SYMMETRY-BASEL VL - 13 PY - 2021 IS - 8 SP - 1516 SN - 2073-8994 DO - 10.3390/sym13081516 UR - https://m2.mtmt.hu/api/publication/32171249 ID - 32171249 N1 - Export Date: 16 February 2022 Correspondence Address: Pálovics, E.; Department of Organic Chemistry and Technology, Hungary; email: palovics.emese@vbk.bme.hu LA - English DB - MTMT ER - TY - JOUR AU - Pálovics, Emese Csilla AU - Bánhegyi, Dorottya Fruzsina AU - Fogassy, Elemér TI - Effect of the Enantiomeric Ratio of Eutectics on the Results and Products of the Reactions Proceeding with the Participation of Enantiomers and Enantiomeric Mixtures JF - CHEMISTRY J2 - CHEMISTRY VL - 2 PY - 2020 IS - 3 SP - 787 EP - 795 PG - 9 SN - 2624-8549 DO - 10.3390/chemistry2030051 UR - https://m2.mtmt.hu/api/publication/31647933 ID - 31647933 N1 - Funding Agency and Grant Number: National Research, Development and Innovation Office-NKFIH through OTKAOrszagos Tudomanyos Kutatasi Alapprogramok (OTKA) [124180] Funding text: This work was supported by the National Research, Development and Innovation Office-NKFIH through OTKA grants 124180 AB - This perspective is focused on the main parameters determining the results of crystallization of enantiomers or enantiomeric mixtures. It was shown that the ratio of supramolecular and helical associations depends on the eutectic composition of the corresponding enantiomeric mixture. The M and P ratios together with the self-disproportionation (SDE) of enantiomers define the reaction of the racemic compound with the resolving agent. Eventually, each chiral molecule reacts with at least two conformers with different degrees of M and P helicity. The combined effect of the configuration, charge distribution, constituent atoms, bonds, flexibility, and asymmetry of the molecules influencing their behavior was also summarized. LA - English DB - MTMT ER - TY - JOUR AU - Varga, Bence AU - Herbay, Réka Gizella AU - Székely, György AU - Holczbauer, Tamás AU - Madarász, János AU - Mátravölgyi, Béla AU - Fogassy, Elemér AU - Keglevich, György AU - Bagi, Péter TI - Scalable Enantiomeric Separation of Dialkyl-arylphosphine oxides based on Host-Guest Complexation with TADDOL-derivatives, and their Recovery JF - EUROPEAN JOURNAL OF ORGANIC CHEMISTRY J2 - EUR J ORG CHEM VL - 2020 PY - 2020 IS - 12 SP - 1840 EP - 1852 PG - 13 SN - 1434-193X DO - 10.1002/ejoc.202000035 UR - https://m2.mtmt.hu/api/publication/31170711 ID - 31170711 N1 - Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3., Budapest, 1111, Hungary Advanced Membranes and Porous Materials Center, Physical Science and Engineering Division (PSE), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955–6900, Saudi Arabia Department of Chemical Engineering and Analytical Science, The University of Manchester, The Mill, Sackville Street, Manchester, M1 3BB, United Kingdom Chemical Crystallography Research Laboratory and Institute of Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2., Budapest, 1519, Hungary Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Szent Gellért tér 4., Budapest, 1111, Hungary Cited By :1 Export Date: 4 February 2021 CODEN: EJOCF Correspondence Address: Bagi, P.; Department of Organic Chemistry and Technology, Műegyetem rkp. 3., Hungary; email: pbagi@mail.bme.hu Funding details: Hawaii Academy of Science, HAS Funding details: OTKA PD 128504 Funding details: King Abdullah University of Science and Technology, KAUST Funding details: National Research, Development and Innovation Office Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH, OTKA PD 116096 Funding text 1: This work was supported by the National Research, Development and Innovation Office - NKFIH (Grant No. OTKA PD 116096). Tam?s Holczbauer is grateful for the support of the National Research, Development and Innovation Office-NKFIH (Grant No. OTKA PD 128504) and the J?nos Bolyai Research Scholarship of the HAS. Gy?rgy Sz?kely acknowledges the financial support from KAUST. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3., Budapest, 1111, Hungary Advanced Membranes and Porous Materials Center, Physical Science and Engineering Division (PSE), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955–6900, Saudi Arabia Department of Chemical Engineering and Analytical Science, The University of Manchester, The Mill, Sackville Street, Manchester, M1 3BB, United Kingdom Chemical Crystallography Research Laboratory and Institute of Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2., Budapest, 1519, Hungary Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Szent Gellért tér 4., Budapest, 1111, Hungary Cited By :1 Export Date: 30 May 2021 CODEN: EJOCF Correspondence Address: Bagi, P.; Department of Organic Chemistry and Technology, Műegyetem rkp. 3., Hungary; email: pbagi@mail.bme.hu Funding details: Hawaii Academy of Science, HAS Funding details: King Abdullah University of Science and Technology, KAUST Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH, OTKA PD 116096 Funding details: National Research, Development and Innovation Office, OTKA PD 128504 Funding text 1: This work was supported by the National Research, Development and Innovation Office - NKFIH (Grant No. OTKA PD 116096). Tam?s Holczbauer is grateful for the support of the National Research, Development and Innovation Office-NKFIH (Grant No. OTKA PD 128504) and the J?nos Bolyai Research Scholarship of the HAS. Gy?rgy Sz?kely acknowledges the financial support from KAUST. LA - English DB - MTMT ER -