- LIC-KOR promoted nitrone reactivity: Stereoselective synthesis of highly conjugated imines and secondary amines
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The reactivity of metalated alkoxy-1,3-dienes and α-aryl-N-phenylnitrones in the presence of LIC-KOR base, equimolar mixture of alkyllithium (LIC) and potassium alcoxides (KOR), (Schlosser, 1994) [1] has been studied. A cascade reaction involving a E1cb p
- Parisotto, Stefano,Boggio, Paolo,Prandi, Cristina,Venturello, Paolo,Deagostino, Annamaria
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- Synthesis of 2′,3′,4′-triaryl-5,6-dihydro-8H-spiro[indolizine-7,5′-isoxazolidin]-8-ones via 1,3-dipolar cycloaddition reaction involving (Z)-C-aryl-N-phenylnitrones
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[Figure not available: see fulltext.] The 1,3-dipolar cycloaddition of C-aryl-N-phenylnitrones to 7-arylmethylidene-6,7-dihydroindolizin-8(5H)-ones afforded novel 2′,3′,4′-triaryl-5,6-dihydro-8H-spiro[indolizine-7,5′-isoxazolidin]-8-ones in moderate yield
- Li, Xiaofang,Li, Youfeng,Tang, Jin
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p. 1062 - 1066
(2020/10/02)
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- Gold-Catalyzed Oxidative Aminocyclizations of Propargyl Alcohols and Propargyl Amines to Form Two Distinct Azacyclic Products: Carbene Formation versus a 3,3-Sigmatropic Shift of an Initial Intermediate
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Gold-catalyzed oxidations of propargyl alcohols with nitrones by using a P(tBu)2(o-biphenyl)Au+ catalyst, afforded bicyclic annulation products from the Mannich reactions of gold enolates. The same reactions of propargyl amines with nitrones by using the same gold catalyst gave distinct oxoarylation products. Our DFT calculations indicate that oxidation of propargyl alcohols with nitrones by using electron-rich gold catalysts lead only to gold carbenes, which can generate gold enolates or oxoarylation intermediates with enolate species having a barrier smaller than that of oxoarylation species.
- Chao, Tzu-Hsuan,Chen, Mu-Jeng,Liu, Rai-Shung,Raj, Antony Sekar Kulandai,Sasane, Amit Vijay
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supporting information
p. 16932 - 16938
(2020/11/30)
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- Synthesis of Exclusively 4-Substituted β-Lactams through the Kinugasa Reaction Utilizing Calcium Carbide
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A new Kinugasa reaction protocol has been elaborated for the one-pot synthesis of 4-substituted β-lactams utilizing calcium carbide and nitrone derivatives. Calcium carbide is thereby activated by TBAF·3H2O in the presence of CuCl/NMI. The ease of synthesis and use of inexpensive chemicals provides rapid access of practical quantities of β-lactams exclusively substituted at position 4.
- Hosseini, Abolfazl,Schreiner, Peter R.
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supporting information
p. 3746 - 3749
(2019/05/24)
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- Catalytic Diastereo- and Enantioselective Synthesis of 2-Imidazolinones
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Chiral cyclic ureas (2-imidazolinones) were prepared by the reaction of nitrones and isocyanoacetate esters using a multicatalytic system that combines a bifunctional Br?nsted base-squaramide organocatalyst and Ag+ as a Lewis acid. The reaction could be achieved with a range of nitrones derived from aryl- and cycloalkylaldehydes with moderate diastereo- and good enantioselectivity. A plausible mechanism involving an initial formal [3 + 3] cycloaddition of the nitrone and isocyanoacetate ester, followed by rearrangement to an aminoisocyanate and cyclization to the imidazolinone, is proposed.
- Martínez-Pardo, Pablo,Blay, Gonzalo,Escrivá-Palomo, Alba,Sanz-Marco, Amparo,Vila, Carlos,Pedro, José R.
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supporting information
p. 4063 - 4066
(2019/06/17)
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- Synthesis and Antimicrobial Evaluation of New Pyrrolo-isoxazolidine Derivatives
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In the present study, pyrrolo-isoxazolidines 3(a-l) and 4(a-e), 4g, 4i, 4j have been synthesized by using the 1,3-dipolar cycloaddition reactions of nitrones 1(a-l) with ester substituted N-aryl maleimide (2b). These heterocycles have been obtained in cis and trans diastereomeric forms. The structures of newly synthesized heterocycles have been confirmed from their spectroscopic parameters such as IR,1H NMR,13C NMR and ESI-MS. The in vitro antimicrobial evaluation of these compounds were also investigated. Most of the prepared heterocycles showed significant antimicrobial properties. C3-phenyl substituted products exhibited the remarkable antibacterial behaviours while C3-thienyl/furyl substituted heterocycles proved themselves potent antifungal agents.
- Yusuf, Mohamad,Shehneela,Singh, Baldev
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p. 220 - 228
(2018/12/11)
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- Coupling of N -Nosylhydrazones with Nitrosoarenes: Transition-Metal-Free Approach to (Z)- N -Arylnitrones
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An efficient and transition-metal-free protocol for the synthesis of (Z)- N -arylnitrones from the direct coupling of N -nosylhydrazones with nitrosoarenes under mild conditions is described. The protocol is compatible with a wide range of functional groups placed on both the reagents and provided the corresponding nitrones in good to excellent yields by simple recrystallization process. The use of these 1,3-dipoles for the synthesis of substituted indoles is elaborated for 2,3-diphenyl-1 H -indole.
- Liu, Tingting,Liu, Zhaohong,Liu, Zhenhua,Hu, Donghua,Wang, Yeming
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p. 1728 - 1736
(2018/02/14)
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- Trifluoromethyl Vinyl Sulfide: A Building Block for the Synthesis of CF3S-Containing Isoxazolidines
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Trifluoromethyl vinyl sulfide, a potential building block for pharmaceutically and agrochemically relevant products, is prepared and used for the first time in high-pressure-mediated 1,3-dipolar cycloaddition reactions with nitrones to synthesize (trifluoromethyl)sulfanyl isoxazolidines.
- Riesco-Domínguez, Alejandra,Van De Wiel, Jeroen,Hamlin, Trevor A.,Van Beek, Bas,Lindell, Stephen D.,Blanco-Ania, Daniel,Bickelhaupt, F. Matthias,Rutjes, Floris P. J. T.
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p. 1779 - 1789
(2018/02/23)
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- Catalytic Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity
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The catalytic formation of gold enolates from alkynes, nitrones, and nucleophiles is described, and their Mannich reactions result in nucleophile-directed chemoselectivity through cooperative catalysis. For 1-alkyn-4-ols and 2-ethynylphenols, their gold-catalyzed nitrone oxidations afforded N-containing dihydrofuran-3(2H)-ones with syn selectivity. The mechanism involves the Mannich reactions of gold enolates with imines through an O-H-N hydrogen-bonding motif. For aryloxyethynes, their gold enolates react selectively with nitrones to deliver 3-alkylidenebenzofuran-2-ones, as controlled by a C-H-O hydrogen-bonding motif.
- Sahani, Rajkumar Lalji,Patil, Manoj D.,Wagh, Sachin Bhausaheb,Liu, Rai-Shung
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supporting information
p. 14878 - 14882
(2018/10/15)
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- Copper-Catalyzed Synthesis of Polysubstituted Pyrroles through [3+1+1] Cycloaddition Reaction of Nitrones and Isocyanides
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An efficient, copper-catalyzed [3+1+1] cycloaddition reaction was developed for the expedient synthesis of pharmacologically interesting polysubstituted pyrroles from easily available nitrones and α-acidic isocyanides. The given approach features a new mo
- Tian, Zhuang,Xu, Jiaojiao,Liu, Bingxin,Tan, Qitao,Xu, Bin
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supporting information
p. 2603 - 2606
(2018/05/22)
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- Chiral: N, N ′-dioxide/Co(II)-promoted asymmetric 1,3-dipolar cycloaddition of nitrones with methyleneindolinones
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A chiral N,N′-dioxide/Co(BF4)2·6H2O complex catalytic system has been developed to efficiently catalyze the asymmetric 1,3-dipolar cycloaddition of nitrones with methyleneindolinones. The corresponding chiral multisubstituted spiroisoxazolidines with three contiguous quaternary-tertiary stereocenters were obtained in moderate to high yields with excellent dr and ee values (up to 97% yield, >19:1 dr and 98% ee).
- Zhang, Dong,Yin, Chengkai,Zhou, Yuhang,Xu, Yali,Lin, Lili,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 7925 - 7928
(2017/07/22)
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- Visible-light-mediated anti-regioselective nitrone 1, 3-dipolar cycloaddition reaction and synthesis of bisindolylmethanes
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The development of photoredox reactions of 1, 3- dipolar cycloaddition of nitrones with alkenes is reported. It offers an efficient synthetic method to obtain isoxazolidine derivatives under mild conditions in synthetically useful yields. The nitrones are cyclized with oxidizable styrenes and aliphatic alkenes via a polar radical crossover cycloaddition reaction through photocatalytic reaction without additives. In addition, bis(indole)methanes can also be prepared through this method.
- Zheng, Lewei,Gao, Fei,Yang, Chao,Gao, Guo-Lin,Zhao, Yating,Gao, Yuan,Xia, Wujiong
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supporting information
p. 5086 - 5089
(2017/11/07)
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- Synthesis of 2,3-Disubstituted NH Indoles via Rhodium(III)-Catalyzed C-H Activation of Arylnitrones and Coupling with Diazo Compounds
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A rhodium-catalyzed intermolecular coupling between arylnitrones and diazo compounds by C-H activation/[4 + 1] annulation with a C(N2)-C(acyl) bond cleavage is reported, and 2,3-disubstituted NH indoles are directly synthesized in up to a 94% yield. A variety of functional groups are applicable to this reaction to give the corresponding products with high selectivity. Compared to other previously reported Rh(III)-catalyzed synthesis of homologous series, this method is simpler, more general, and more efficient.
- Guo, Xin,Han, Jianwei,Liu, Yafeng,Qin, Mingda,Zhang, Xueguo,Chen, Baohua
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p. 11505 - 11511
(2017/11/10)
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- Synthesis of Benzimidazolones via One-Pot Reaction of Hydroxylamines, Aldehydes, and Trimethylsilyl Cyanide Promoted by Diacetoxyiodobenzene
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A novel and efficient PhI(OAc)2-promoted one-pot reaction of aromatic hydroxylamines, aldehydes, and TMSCN in the presence of BF3·Et2O is described. A wide variety of N-substituted benzimidazolones are obtained with satisfactory yields under mild reaction conditions. The method was proven to be efficient for the synthesis of benzimidazolone derivatives from readily available starting materials.
- Zhang, Huaiyuan,Huang, Danfeng,Wang, Ke-Hu,Li, Jun,Su, Yingpeng,Hu, Yulai
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p. 1600 - 1609
(2017/02/10)
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- Nickel(II)-Catalyzed Enantioselective 1,3-Dipolar Cycloaddition of Nitrones with α,β-Unsaturated Acylcarboxylates
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The highly enantioselective 1,3-dipolar cycloaddition of nitrones with α,β-unsaturated acylcarboxylates was realized for the first time by using a chiral bis(indano-oxazoline)-based Ni complex. The reaction proceeded smoothly under mild conditions and provided isoxazolidines with three contiguous stereocenters in high yields with excellent diastereoselectivities (>20:1 dr) and enantioselectivities (up to 99 % ee). The reaction was scaled up to the gram scale, and the products were readily transformed into γ-amino alcohols and other potentially bioactive compounds.
- Xie, Lei,Yu, Xuan,Li, Jiaqi,Zhang, Zhenhua,Qin, Zhaohai,Fu, Bin
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supporting information
p. 657 - 661
(2017/02/05)
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- Cu(II)-catalyzed enantioselective 1,3-dipolar cycloaddition of nitrones with α, β-unsaturated acyl phosphonates
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A highly enantioselective 1, 3-dipolar cycloaddition of nitrone with α, β-unsaturated acyl phosphonate was developed for the first time by using a chiral indane-bis(oxazoline)-copper(II) complex. The reaction proceeded smoothly under mild conditions to provide isoxazolidines with multi-stereocenters in good yields with high to excellent diastereo- (>20:1 dr) and enantioselectivities (up to 99% ee). The resulting products were readily converted to multi-functional isoxazolidines or γ-amino alcohol compounds.
- Xie, Lei,Bai, Hui,Li, Jiaqi,Yu, Xuan,Zhang, Zhenhua,Fu, Bin
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supporting information
p. 2923 - 2930
(2017/04/27)
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- Influence of the side-group at C=N bridging bond of bis-aryl Schiff bases on the wavelength of absorption maximum of ultraviolet absorption spectra
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The compounds N-(benzylidene)-anilines XArCH=NArY (XBAY), N-(phenyl-ethylene)-anilines XArC(CH3)=NArY (XPEAY) and N-phenyl-α-phenylnitrones XArCH=N(O)ArY (XPNY) have bridging group CH=N, C(CH3)=N and CH=N(O) respectively, in which the C(CH3)=N has a side-group methyl CH3 at carbon end and the CH=N(O) has a side-group O atom at nitrogen end. In this work, a series of XPEAY and XPNY were synthesized, and their longest wavelength maximum λmax (nm) of ultraviolet absorption spectra were measured. Then the change regularity of the νmax (cm-1, νmax=1/λmax) of XPEAY and XPNY were investigated, and they were compared with that of XBAY (reported by ref.26). The results indicate: (1) There are no good linear relationships between the νmax of XBAYs and XPEAYs or XPNYs. (2) In case of a same set of X-Y group couples, the distribution of λmax of XPEAYs is larger than that of XPNYs. (3) The side-group CH3 makes the effect of σ(X) larger than that of σ(Y) on the νmax of XPEAYs, whereas the O atom makes the effect of σ(Y) larger than that of σ(X) on the νmax of XPNYs. (4) The cross-interaction between X and Y has important effect on the all νmax. However, the cross-interaction between CH3 and X/Y has not important effect on the νmax of XPEAY, and the cross-interaction between O and X/Y has not important effect on the νmax of XPNY. Copyright
- Luo, Qingqing,Cao, Chao-Tun,Cao, Zhongzhong,Cao, Chenzhong
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p. 406 - 413
(2016/07/28)
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- Iron-Catalyzed Cyclization of Nitrones with Geminal-Substituted Vinyl Acetates: A Direct [4 + 2] Assembly Strategy Leading to 2,4-Disubstituted Quinolines
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An iron-catalyzed intermolecular [4 + 2] cyclization of arylnitrones with geminal-substituted vinyl acetates was developed for the synthesis of 2,4-disubstituted quinolines in moderate to good yields with good functional group compatibilities. Preliminary mechanistic studies suggest a plausible iron-catalyzed C-H activation process under external-oxidant-free conditions.
- Zhong, Mingbing,Sun, Song,Cheng, Jiang,Shao, Ying
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p. 10825 - 10831
(2016/11/29)
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- An unexpected catalytic synthesis of novel and known bis(pyrazolyl) methanes by the use of α-aryl-N-phenyl nitrones in aqueous media
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Reaction of -aryl-N-phenyl nitrones with 3.methyl-1-phenyl-2-pyrazoline-5-one in the presence of a catalytic amount of silica tungstic acid in EtOH/H2O afforded, unexpectedly, high yields of bis(3-hydroxy-1-phenylpyrazolyl)-arylmethanes instead of the two possible 1,3-addition products. This is the first report of the synthesis of bis(3-hydroxy-1-phenylpyrazolyl)-arylmethanes via the reaction of nitrones and a pyrazolin-5-one. A possible mechanism for the process is suggested.
- Eskandari, Khalil,Karami, Bahador,Khodabakhshi, Saeed
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p. 600 - 603
(2014/12/12)
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- Urea-catalyzed construction of oxazinanes
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Highly functionalized oxazinanes are efficiently prepared through urea-catalyzed formal [3 + 3] cycloaddition reactions of nitrones and nitrocyclopropane carboxylates. The reaction system is general with respect to both the nitrocyclopropane carboxylates and nitrones enabling the preparation of a large family of oxazinanes, typically in high yield. This method affords access to enantioenriched oxazinane products through chirality transfer from enantioenriched nitrocyclopropane carboxylates.
- Hardman, Andrea M.,So, Sonia S.,Mattson, Anita E.
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supporting information
p. 5793 - 5797
(2013/09/12)
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- Synthesis and evaluation of hexahydropyrrolo[3,4-d]isoxazole-4,6-diones as anti-stress agents
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A series of 2,3-diphenyl-5-(naphthalen-1-yl)-4H-2,3,3a,5,6,6a- hexahydropyrrolo[3,4-d]isoxazole-4,6-dione derivatives were synthesized via 1,3-dipolar cycloaddition of azomethine N-oxides with N-(α-naphthyl) maleimide. The pyrrolo-isoxazole derivatives were assigned cis- and trans- configurations (3-A and 3-B) with respect to proton C3-H on azomethinic carbon on the basis of their 1H NMR. The reaction proceeds through cis- endo addition rule indicating the predominance of cis isomer. The cis- and trans- isomers of a prototype compound 3a i.e., compound 3a-A and compound 3a-B were evaluated for anti-stress activity in immobilization-induced acute stress. Compound 3a-A (5 and 10 mg/kg) and compound 3a-B (10 mg/kg) attenuated immobilization stress-induced behavioral alterations in Swiss albino mice suggesting that pyrrolo-isoxazole may serve as lead molecule for the development of anti-stress agents.
- Badru, Rahul,Anand, Preet,Singh, Baldev
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experimental part
p. 81 - 91
(2012/03/22)
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- Copper(I)-catalyzed three component reaction of sulfonyl azide, alkyne, and nitrone cycloaddition/rearrangement cascades: A novel one-step synthesis of imidazolidin-4-ones
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A novel one-pot azide-alkyne/ketenimine-nitrone cycloaddition sequence that is induced by copper(I) and allows the transformation of sulfonyl azides, alkynes, and nitrones to highly substituted imidazolidin-4-ones is described. The corresponding heterogeneous version utilizing Cu(I)-modified zeolites as recyclable heterogeneous catalysts shows marginally improved yield and diastereoselectivity.
- Namitharan, Kayambu,Pitchumani, Kasi
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supporting information; body text
p. 5728 - 5731
(2011/12/05)
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- Regio-and stereoselective 1,3-dipolar cycloaddition of C-aryl-N- phenylnitrones over (E)-arylidene-(2H)-indan-1-ones: Synthesis of highly substituted novel spiro-isoxazolidines
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Synthesis of a series of novel spiro-isoxazolidines has been accomplished in good yields by regio-and diastereoselective 1,3-dipolar cycloaddition of (E)-2-arylidene-(2H)-indan-1-ones 1a-d to C-aryl-N-phenylnitrones 2e-h. The structure of the spiro-adduct
- Wannassi, Nadia,Rammah, Mohamed Mehdi,Boudriga, Sarra,El Baker Rammah, Mohamed,Monnier-Jobe, Karin,Ciamala, Kabula,Knorr, Michael,Enescu, Mironel,Rousselin, Yoann,Kubicki, Marek M.
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body text
p. 2749 - 2762
(2011/04/16)
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- Studies of multicomponent Kinugasa reactions in aqueous media
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Micelle-promoted, copper-catalyzed multicomponent Kinugasa reactions were studied in aqueous media. Reactions were performed in a 'single pot' for a series of in situ generated C,N-diphenylnitrones with Cu(I) phenylacetylide providing β-lactams in yields of 45-85%. Substituents affect the reaction by either accelerating cycloaddition or minimizing side reactions.
- McKay, Craig S.,Kennedy, David C.,Pezacki, John Paul
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supporting information; experimental part
p. 1893 - 1896
(2009/07/05)
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- Synthesis and bioorthogonal coupling chemistry of a novel cyclopentenone-containing unnatural tyrosine analogue
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Herein we report the synthesis of a novel amino acid with orthogonal functionality to the natural amino acid side chains. Tyrosine was O-alkylated with a cyclic 5-membered α,β-unsaturated ketone ring (5). We have established that this amino acid analogue can undergo cycloaddition reactions in aqueous media with in situ generated nitrones. Nitrone formation occurred by micellar catalysis can undergo aqueous 1,3-dipolar cycloaddition reactions with the unnatural Tyr. We also performed a linear free energy analysis of the one pot bioconjugation reaction in water using cyclopentenone as a model for the Tyr analogue and seven different aryl nitrones. We found that the Hammett ρ value was -0.94, suggesting that the reaction occurs in a concerted fashion with a slight positive charge buildup in the transition state. The Hammett ρ value also suggests that the bioconjugation reaction is tolerant of different substituents and thus may be useful for introducing novel functionality into peptides and proteins containing the Tyr analogue 5. The aqueous 1,3-dipolar cycloaddition reactions, that use nitrones to trap the O-alkylated Tyr 5, establish a novel strategy for rapid, water compatible bioconjugation reactions.
- Lorello, Gianni R.,Legault, Marc C.B.,Rakic, Bojana,Bisgaard, Kathrine,Pezacki, John Paul
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p. 105 - 111
(2008/09/19)
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- Synthesis of C, N-diaryl nitrones from the reduction of nitroarene with aromatic aldehydes promoted by metallic samarium
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A mild and facile reduction of nitroarene with aromatic aldehydes promoted by metallic samarium to C, N-diaryl nitrones in moderate yields has been developed.
- Jia, Xueshun,Li, Dafeng,Huang, Qing,Zhu, Li,Li, Jian
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p. 308 - 309
(2008/02/08)
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- Microwave mediated synthesis of spiro-(indoline-isoxazolidines): Mechanistic study and biological activity evaluation
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Regioisomeric spiro-(indoline-isoxazolidines) have been synthesized in moderate yields by the cycloaddition reaction between ethyl (3-indolylidene) acetate and various substituted α,N-diphenylnitrones, using environmentally benign microwave technology. A
- Raunak,Kumar, Vineet,Mukherjee, Shubhasish,Poonam,Prasad, Ashok K.,Olsen, Carl E.,Sch?ffer, Susan J.C.,Sharma, Sunil K.,Watterson, Arthur C.,Errington, William,Parmar, Virinder S.
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p. 5687 - 5697
(2007/10/03)
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- 1,3-Dipolar cycloaddition reactions of nitrones to prop-1-ene-1,3-sultone
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The reaction of prop-1-ene-1,3-sultone (1) with a variety of nitrones 2 afforded novel [3+2] cycloaddition products 3, 4, and 5 in good yield. Excellent regio- and stereoselectivity were achieved in the cycloaddition reaction with phenylnitrones.
- Tian, Li,Xu, Guo-Yan,Ye, Yong,Liu, Lun-Zu
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p. 1329 - 1334
(2007/10/03)
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- Regio- and stereoselectivity of captodative olefins in 1,3-dipolar cycloadditions. A DFT/HSAB theory rationale for the observed regiochemistry of nitrones
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Captodative olefins 1-acetylvinyl carboxylates proved to be highly regioselective dipolarophiles in 1,3-dipolar cycloadditon to propionitrile oxide, arylphenylnitrile imines, diazoalkanes, and nitrones to yield the corresponding 5-substituted heterocycles
- Herrera,Nagarajan,Morales,Mendez,Jimenez-Vazquez,Zepeda,Tamariz,Tamariz
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p. 1252 - 1263
(2007/10/03)
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- Oxygenation of aldimines and deoxygenation of nitrones on irradiated TiO2
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While aldimines have boca selectively oxidized to nitrones in TiO2 suspended acetonitrile solution in the presence of O2 upon irradition, nitrones are reduced to their deoxygenated derivatives with retention of C=N by TiO2 photocatalysis under a nitrogen atmosphere.
- Somasundaram,Srinivasan
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p. 3547 - 3550
(2007/10/03)
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- A clean clay catalysed synthesis of α,N-diarylnitrones
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The first clean and the facile clay catalysed synthesis of α,N-diarylnitrones in good yield is reported.
- Venkatachalapathy, Chockalingam,Thirumalaikumar, Muniappan,Muthusubramanian, Shanmugam,Pitchumani, Kasi,Sivasubramanian, Shunmugaperumal
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p. 4041 - 4047
(2007/10/03)
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- ?-? Molecular Complexes with Nitrones: PartIV - Substituent Effect in the Complexation of Aryl Nitrones with Tetracyanoethylene and 1,4-Benzoquinones
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Charge-transfer complexes of some substituted nitrones with tetracyanoethylene and 1,4-benzoquinones have been studied spectrophotometrically.The stoichiometry and apparent formation constants of the complexes have been determined.From the energies of the charge-transfer transitions, the ionization potentials of the donors have been obtained.
- Nour El-Din, Ahmed M.
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p. 511 - 512
(2007/10/02)
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