{"title":"Synthesis of stable 1,4-diionic organophosphorus compounds from the reaction between triphenylphosphine and diaroylacetylenes in the presence of 5-aryl-4-quinoxalin-2-yl-furan-2,3-diones","authors":"N. Y. Lisovenko, A. V. Dryahlov, M. V. Dmitriev","doi":"10.1080/10426507.2017.1295962","DOIUrl":"https://doi.org/10.1080/10426507.2017.1295962","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT Novel 1,4-diionic organophosphorus compounds have been obtained efficiently from the one-pot three-component reaction of triphenylphosphine, diaroylacetylenes and 5-aryl-4-quinoxalin-2-yl-furan-2,3-diones in 1,2-dichloroethane. The synthesized compounds were characterized by different spectroscopic methods and their structure was confirmed in one case by single crystal X-ray diffraction.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"56 1","pages":"950 - 953"},"PeriodicalIF":0.0,"publicationDate":"2017-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79352303","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
M. Gerova, Filip E. Svetoslavov, B. Shivachev, R. Nikolova, O. Petrov
{"title":"Synthesis of 4-acetyl-2(3H)-benzothiazolone: Sulfur bioisostere of benzoxazolone allelochemicals","authors":"M. Gerova, Filip E. Svetoslavov, B. Shivachev, R. Nikolova, O. Petrov","doi":"10.1080/10426507.2017.1321645","DOIUrl":"https://doi.org/10.1080/10426507.2017.1321645","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT A multi-step methodology for the synthesis of 4-acetyl-2(3H)-benzothiazolone was developed in order to prepare a new biomimetic analogue of benzoxazolone allelochemicals. The compound was prepared from commercially available o-toluidine in 23% overall yield. The structure of 4-acethyl-2(3H)-benzothiazolone was confirmed by NMR spectroscopy and X-ray crystallography.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"77 1","pages":"905 - 910"},"PeriodicalIF":0.0,"publicationDate":"2017-04-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76178683","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Microemulsion and macroemulsion polymerization of octamethylcyclotetrasiloxane: A comparative study","authors":"J. Khanjani, M. Zohuriaan‐Mehr, S. Pazokifard","doi":"10.1080/10426507.2017.1315418","DOIUrl":"https://doi.org/10.1080/10426507.2017.1315418","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT Octamethylcyclotetrasiloxane (D4) was polymerized in a microemulsion system using novel formulations, in which acrylamide was involved as a co-emulsifier. Dodecylbenzene sulfonic acid was used as both a cationic initiator and emulsifier. The effect of emulsifiers, D4, feeding rate and temperature on conversion, polymerization rate (Rp), latex stability and particle sizes were investigated. A conventional (macroemulsion) system was also studied comparatively. Rp in the microemulsion was quickly increased to a maximum of 0.108 mol L−1s−1 at ∼30 min corresponding to a conversion of ∼38%, and then decreased with reaction progression over a period of 30–110 min. In the macroemulsion system, however, a constant rate was observed between conversion 30% and 50%, and its optimal sample contained an average particle diameter of 88 nm while that from microemulsion had smaller particles with diameter of 19 nm. Activation energies were also estimated to be 31.5 and 41.1 kJ/mol for the microemulsion and macroemulsion systems, respectively.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"259 1","pages":"967 - 976"},"PeriodicalIF":0.0,"publicationDate":"2017-04-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76629349","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Improved synthesis of N-sulfonylformamidine derivatives promoted by thionyl chloride","authors":"Ruzeahong Hudabaierdi, Abudureheman Wusiman, Ayinigeer Mulati","doi":"10.1080/10426507.2017.1284843","DOIUrl":"https://doi.org/10.1080/10426507.2017.1284843","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT An improved synthesis of N-sulfonylformamidine derivatives has been developed involving direct condensation of various sulfonamides and formamides in the presence of thionyl chloride using chloroform as solvent. Detailed synthetic studies indicate that this procedure gives the desired products in high yields under mild conditions.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"353 1","pages":"485 - 489"},"PeriodicalIF":0.0,"publicationDate":"2017-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77321162","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Some introductory remarks to “In memoriam of Prof. Harry R. Hudson”","authors":"G. Hägele","doi":"10.1080/10426507.2017.1300034","DOIUrl":"https://doi.org/10.1080/10426507.2017.1300034","url":null,"abstract":"Phosphoros–the Morningstar, what a wonderful world came down to us through the millennia–let us keep and protect it! And Harry Hudson was able to wander between the worlds of arts and science as well. His advice in English history and literature was well accepted, like his profound knowledge in chemistry. We teamed up as partners in a group of chemists named EUROPHOS and combined our labs in London and in Düsseldorf with syntheses, analytics, structures, NMR spectroscopy and biological aspects. We enjoyed mutual visits, supported by binational funds, and looked into α-aminophosphonic acids, α-aminophosphinic acids and corresponding esters, generally abbreviated as NHR1-CHR2-P(O)(R3)OR4. Selected results were published in a review, edited by V. Khukar and H. R. Hudson1 and in several publications.2a–j Molecular modelling, ring current calculations, and NMR were combined to understand complex 1H NMR spectra of NHPh-CHPh-P(O(OEt)2 and related structures.3 Compounds with sterically demanding substituents NH(CHPh2)-CHR-P(O(OEt)2 (R2 = Ph, Naphthyl, Anthranyl, Pyrenyl) were synthesized.4a–b Our particular interests were drawn toward the sterically overcrowded α-N-(diphenylmethyl)amino-α-(1-pyrenyl)methanephosphonic acid diethylester NH(CHPh2)-CH (Pyr)-P(O(OEt)2 which gave rise to a 1H NMR spectrum5 (Figure 1) involving a total of 29 spins (Scheme 1):","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"48 5 1","pages":"578 - 580"},"PeriodicalIF":0.0,"publicationDate":"2017-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82764680","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Triphenylarsine as an effective catalyst in a mechanistic investigation of trans- 1, 2-di (methoxycarbonyl)-6, 6-dimethyl-5, 7-dioxaspiro [2, 5] octane-4, 8-dione formation","authors":"F. Ghodsi, S. Habibi‐Khorassani, M. Shahraki","doi":"10.1080/10426507.2017.1302448","DOIUrl":"https://doi.org/10.1080/10426507.2017.1302448","url":null,"abstract":"ABSTRACT The kinetics and mechanism of the reaction between dimethyl acetylendicarboxylate (DMAD) and Meldrum's acid (MA) in the presence of triphenylarsine (TPA) as a catalyst were investigated in a methanol environment by the UV/vis spectrophotometry technique. In this work, the reaction followed second- order kinetics and the first and second steps of the reaction mechanism were recognized as the fast and rate-determining step (RDS), respectively. A significant point in this reaction “in comparison with previous work” is related to the change in behavior of the kinetics and reaction mechanism in the presence of triphenylarsine (TPA). Activation energy and parameters (Ea, ΔH‡, ΔS‡, and ΔG‡) were determined for the reaction and a comparison between ΔH‡ and TΔS‡ values showed that the reaction is entropy-controlled. High values of the activation Gibbs free energy indicated that the reaction was chemically controlled. Also, the large negative value of ΔS‡ implied an associative mechanism. GRAPHICAL ABSTRACT","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"Suppl 1","pages":"960 - 966"},"PeriodicalIF":0.0,"publicationDate":"2017-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90229647","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Recalling my memories with Professor Harry R. Hudson","authors":"G. Keglevich","doi":"10.1080/10426507.2017.1296732","DOIUrl":"https://doi.org/10.1080/10426507.2017.1296732","url":null,"abstract":"","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"36 1","pages":"581 - 581"},"PeriodicalIF":0.0,"publicationDate":"2017-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73582100","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"The first C(O)NHP(O)-based phosphoric triamide structure with an N‒H···π hydrogen bonding: A combination of X-ray crystallography and theoretical study to evaluate the strength of hydrogen bonds","authors":"M. Taherzadeh, M. Pourayoubi, R. Afzali, M. Nečas","doi":"10.1080/10426507.2017.1295960","DOIUrl":"https://doi.org/10.1080/10426507.2017.1295960","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT The hydrogen bond pattern of N-(4-methoxybenzoyl)-N′,N″-bis(4-methylbenzyl)-phosphoric triamide, C24H28N3O3P, (I), was investigated. In the crystal structure, the molecules are aggregated through NCP―H···O═P and NP―H···O═C hydrogen bonds in a one-dimensional arrangement parallel to the c axis (NCP is the nitrogen atom in the C(O)NHP(O) segment and NP stands for the two other nitrogen atoms bonded to the P atom). There is also a novel NP‒H···π hydrogen bond in the crystal which extends the aggregation of the molecules to a two-dimensional array parallel to the bc plane. A Cambridge Structural Database (CSD, version 5.37, Feb 2016) analysis shows that the N―H···π hydrogen bond was not observed in any of 156 [RC(O)NH]P(O)[NR1R2]2 (R1 ≠ H, R2 = H or ≠ H) phosphoric triamide structures reported so far. The theoretical calculations at the B3LYP/6-311G** level of theory (DFT, AIM, and NBO) were performed to evaluate the strengths of NCP―H···O═P, NP―H···O═C and NP―H···π hydrogen bonds, considering two-aggregate molecular assemblies containing these hydrogen bonds. The calculations on the title compound suggest that the intermolecular NCP―H···O═P hydrogen bond is stronger than NP―H···O═C and NP―H···π interactions. The hydrogen bond strength was investigated by NBO, topological analysis, geometry calculation, Hirshfeld surface analysis and experimental spectroscopic results, which are in agreement with each other.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"202 1","pages":"936 - 944"},"PeriodicalIF":0.0,"publicationDate":"2017-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75678933","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
F. Ghodsi, M. Shahraki, S. Habibi‐Khorassani, Maryam Shokoohian
{"title":"The comparison of the dynamic 1H NMR measurements between two special ylides derived from triphenylphosphine and triethylphosphite: Experimental and theoretical calculations","authors":"F. Ghodsi, M. Shahraki, S. Habibi‐Khorassani, Maryam Shokoohian","doi":"10.1080/10426507.2017.1292274","DOIUrl":"https://doi.org/10.1080/10426507.2017.1292274","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT Dynamic 1H NMR measurements have been experimentally performed in particular phosphorus ylides involving 2-mercaptobenzimidazole and 2-mercaptobenzoxazole for comparison around the C˭C double bond and two single bonds (C‒C and C‒N). Also, activation parameters including ΔG‡, ΔS‡ and ΔΗ‡ were calculated using the ab initio and DFT methods at the HF/6-31G (d,p) and B3LYP/6-31G(d,p) levels of theory for the rotational interchangeable process of the two Z and E isomers of the ylides in the presence of a solvent environment (CDCl3). The obtained results were consistent with the dynamic 1H NMR data. The rotational energy barrier around the carbon=carbon double bond in the ylide 4 derived from triphenylphosphine was 2 kcal⋅mol−1 higher in energy than the generated ylide 5 from triethylphosphite. In general, in both rotational Z and E isomers of ylide 5, the rotational energy barrier around the carbon–nitrogen single bond was higher for the carbon‒carbon single bond due to the inversion of a lone pair on nitrogen atom during a rotation. Although, the HF/6-31G(d,p) level was a desirable level for the rotation around the single bond, nevertheless, the B3LYP/6-31G(d,p) level was recognized as a suitable level for rotation around the double bond. Applying solvent media (chloroform) at the two levels of calculations increased consistency with the experimental results.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"94 1","pages":"929 - 935"},"PeriodicalIF":0.0,"publicationDate":"2017-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90723992","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
H. Yarahmadi, M. Ghashang, Saeid Jabbar Zare, A. Khodaivandi
{"title":"Barium aluminate nano-powders efficient catalyst for the synthesis of novel benzo[b]thiophene, thieno[2,3-c]thiopyran and thieno[2,3-c]pyridine derivatives","authors":"H. Yarahmadi, M. Ghashang, Saeid Jabbar Zare, A. Khodaivandi","doi":"10.1080/10426507.2017.1295961","DOIUrl":"https://doi.org/10.1080/10426507.2017.1295961","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT Uniform nanopowders of barium aluminate (BaAl2O4) can be synthesized by a facile solution reaction at room temperature using barium and aluminum salts and 2-aminoethanol as a precipitating agent. The as-prepared sample showed a good reactivity in the synthesis of benzo[b]thiophene, thieno[2,3-c]thiopyran and thieno[2,3-c]pyridine derivatives. Comparatively the method is efficient and eco-friendly, and finally, a range of compounds with variable functionalities in excellent yield can be achieved.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"15 1","pages":"945 - 949"},"PeriodicalIF":0.0,"publicationDate":"2017-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88363980","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}