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Kinetic Study on Bromine-Exchange Reaction of Antimony Tribromide with F-Butyl Bromide in Nitrobenzene and in 1,2,4-Trichlorobenzene*

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Kinetic Study on Bromine-Exchange Reaction of Antimony Tribromide with F-Butyl Bromide in Nitrobenzene and in 1,2,4-Trichlorobenzene* 144 Bulletin of Korean Chemical Society, Vol. 3, 시 。. 4, 1982 Sang Up 아 loi and Young 11 Pae Substitution of approximate values, ^=0.8 hartrees,12 Ac 6137 (1981). =0.06 hartrees,13 sW0.089(for trans overlap)12 and 5^0.072 (2) M. J. S. Dewar and R. C. Dougherty. "The PMO Theory of Org. 아 】em.," Plenum Press, New York, 1975. (for cis overlap),12 into 一쯔一 =2(쓰 ) indicates that (3) (a) K. F니 k니 i, T. Yonezawa and H. Shingu, J. Chem. Phys., 20, 722 (1952); (b) I. Fleming, "Fronti히 Orbitals and and eav—is always negative. However is Org. Chem. Reactions", John Wiley, London, 1976. (4) (a) C. Sandorfy and R. Da나 del. Comp. Rend., 238, 93 approximately 2.82 for trans while it is 1.84 for cis reducing (1954); (b) W. C. Herndon, "Prog. Phys. Org. Chem.", the magnitude of €av-€0 for the cis to approximately 2/3 9, 99 (1972); (c) M. N. Paddon-Row, H. K. Patney. R. S. of that for the trans. Brown and K. N. Houk, J. Amer. Chem. Soc.f 103, 5575 The average, eav, is always lower than the basis level e0 (1981); (d) J. W. Verhoeven and P. Pasman, Tetrahedron, in eq. (18), irrespective of whether the N is odd or even. 37, 943 (1981). Moreover according to eq. (18), through-space dominated (5) (a) L. Libit and R. Hoffmann, J. Amer. Chem. Soc., 96, (destabilizing) interaction is not possible. This absurdity is 1370 (1974); (b) S. Inagaki, H. Fujimoto and K. F니 oji, of course a result of the approximation that x=y. ibid.. 98, 4693 (1976), Photoelectron spectroscopic datale included in Table 3 (6) A. D. B니 ckingham, Tnterm이 ec비 ar Interactions'1, ed. are in full accord with our predictions: (i) the nitrogen atoms Chapt. 1. B. Pulman, Johu Wiley, New York, 1978. in 1,6-diazabicyclo (4.4.4) tetradecane must be inwardly (7) This corresponds to adopting the PT 1 procedure of pyramidalized increasing the direct overlap so that the in­ Hoffmann et a/.la teraction is through-space dominated and is destabilizing, (8) The c0 is also raised 이 ightly as the N increases (Table 1). 6av>fo, (ii) interactions in the other two diazabicyclo This may be d니 e to the decrease in the magnitude of compounds are through-bonds dominated and are stabiliz­ electrostatic (attraction) energy, |e'|, since the net 아 】arge ing, fav<f0, (iii) energy splitting, AE, for N=odd (DA density of the framework 아 io니 d decrease with the size, BCO) is larger than that for TV even [1,5-diazabicyclo i. e.r with the increase in the N. (3.3.3) undecane] even allowing for the increase in N by 1. (9) (a) N. D. Epiotis, R. L. Yates, J. R. Larson, C. R. Kirmaier Acknowledgement. We thank the Ministry of Education and F. Bernardi, J. Amer. Chem. Soc., 99, 8379 (1977); and the Korea Research Center for Theoretical Physics (b) T. K. Brunck and F. Weinhold, ibid., 101,1700 (1979). and Chemistry for support of this Work. (10) W. T. Borden and E. R. Davidson, ibid., 102, 5409 (1980). References (11) Note 廿 lat S is for the direct overlap between m and n2 while s is for the overlap detween n 히 id framework(7 (1) (a) R. Hoffmann, A. Imamura and W. J. Hehre, J. Amer. orbitals. Chem. Soc., 90, 1499 (1968); (b) A. Imamura and K. (12) These are overlap integrals for Hamiltonian matrix elements Hirao, Bull. Chem. Soc. Japan, 51, 3443 (1978): (c) E. Hnt; and <0n|%h〉； 丁 . K. Brunck and F. Weinh이 d, Heilbronner and K. A. M니 szkat, J. Amer. Chem. Soc., 92, J. Amer. Chem. Soc., 98, 3745 (1976). 3818 (1970); (d) E. Heilbronner and A. Schmelzer, Helv. (13) The ''C-Approximatk)n'' gives HOMO energies ranging Chim. Acta, 58, 936 (1975); (e) R. W. Alder, R. J. Arrow­ O.O52~O.O62a.u. for /V = 2〜assuming ^=2eV.14 smith, A. Casson, R. B. Sessions, E. heilbronner, B. Kovac, (14) Ref. (2), p.363. H. Huber and M. Taagepera, J. Amer. Chem. Soc., 103, Kinetic Study on Bromine-Exchange Reaction of Antimony Tribromide with f-Butyl Bromide in Nitrobenzene and in 1,2,4-Trichlorobenzene* Sang Up Choit and Young II Pae** Department of Chemistry, Sogang University, Seoul 121f Korea (Received March. 10r 1982) The kinetic study on the bromine-exchange reaction of antimony tribromide with z-butyl bromide in nitrobenzene or 1,2,4- trichlorobenzene has been carried out, using Br-82 labelled antimony tribromide. The results show that the exchange reac­ tion is first order with respect to /-butyl bromide and 1.5th order with respect to antimony tribromide. It is assumed that the 1.5th order indicates the coexistance of first -and second-order kinetics. Reaction mechanisms for the exchange reac­ tion are proposed. ♦Abstracted, in part, from Ph. D. thesis of Y이 mg II Pae, Sogang University, 1979. ♦♦Present Address: Department of Industrial Chemistry, Ulsan Institute of Technology, Ulsan, Korea. Bromine Exchange Reaction of SbBr3 with r-C4HgBr Bulletin of Korean Chemical Society, Vol. 3, No. 4. 1982 145 phorus tribromide drop by drop. Thus, /-butyl bromide Introduction was synthesized, and it was purified by fractionation. Experimental Procedures for Kinetic Studies. The experi­ We have recently investigated the kinetic study on the mental procedures for kinetic study of the bromine-exchange bromine-exchange reaction between antimony tribromide reaction were the same as those described in the previous and benzyl bromide in nitrobenzene or 1,2,4-trichlorobenzene, paper.1 The rate of the exchange reaction was calculated by using Br-82 labelled antimony tribromide.1 The result of the following equation9: the study indicated that the rate of the exchange reaction was first order with respect to benzyl bromide, and was either Rate=—2.303(潔 厂)务 庇 (会三쓰 ) ⑷ second or first order with respect to antimony tribromide depending on its concentrations. In this equation a denotes the molar concentration of anti­ Rate=^3(C6H5CH2Br] [SbBr3]2 mony tribromide, b that of /-butyl bromide, and At and (at higher (SbBr3) concentrations) (1) L the radioactivities of the organic layer at time zero, at time Rate = k2 [C6H5CH2Br] [SbBr3] t, and at time of the completion of the exchange reactions, (at lower [SbBr3J concentrations) (2) respectively. These two rate expressions were interpreted by two different The values of 丄 were obtained by the following equation: rea아 ion mechanisms. 4。。=盘'/弘 "1 On the other hand, as the results of similar studies on the systems of gallium bromide with alkyl bromides, we reported that the bromine-exchange reactions of gallium bromide where /£而 1 denotes the total radioactivity present in both with alkyl bromides followed simpler kinetics, i.e., first order organic and aqueous layers. Then, the values of log ((— with respect to the organic bromides and second order with 厶， / (刀 8一 厶0)} were plotted against time t. From the slope respect to gallium bromide.2-7 of the plots, the rate of the exchange reaction was calculated by equation (4). Rate=妫〔RBr〕(GaBr3)2 (3) Results These two systems with different metal bromides and different Bromine-Exchange Reaction of Antimony Tribromide with organic bromides indicated fairly large difference in reaction t-Butyl Bromide in Nitrobenzene. The rates of bromine ex­ kinetics of the bromine-exchange reactions. It appeared of change between antimony tribromide and Z-butyl bromide interest to try to clarify whether the difference in kinetics in nitrobenzene were measured with various concentrations was ascribed to the properties of different metal bromides or of both antimony tribromide and /-butyl bromide. In each those of organic bromides. It was hoped to extend the exchan­ run of the experiments, good linearity was observed between ge studies to the system of antimony tribromide with simpler log{(瓦 。一 &)/(瓦 。— 瓦 )} and /. From the slope of the alkyl bromides such as methyl and ethyl bromides. It has been plots and molar concentrations of antimony tribromide observed that antimony tribromide exchanges bromine atoms and z-butyl bromide, the exchange rate was calculated by with alkyl bromides much more slowly than gallium bromide.8 equation (4). The results are summarized in Ta비 es 1 and 2. Thus, ^-butyl bromide was chosen as alkyl bromide in this Table 1 shows the data obtained at given [SbBr3] concent­ experiment because /-butyl bromide was thought to be gener­ ration, and Table 2 the data at givenC4H9BH concen­ ally more reactive than methyl and ethyl bromides. The pre­ tration. sent study was undertaken on the system of antimony tri­ The rate of the exchange reaction was expressed by the bromide with C-butyl bromide in nitrobenzene or 1,2,4- trichlorobenzene. TABLE 1: Rates of Exchange of Bromine between Antimony Tri- Experiment이 Part bromide and ^-Butyl Bromide at Given (SbBr3) Concentration in Nitrobenzene. Materials. The solvents used in the present study were purified by the method described in the previous paper.1 Temp. [SbBr3] X 102 Cr-C4H9Br] X102 RateX 107 mole JT mole-Z-1-sec"1 Radioactive antimony tribromide labelled with Br-82 °C mole/'1 was prepared by the method reported previou시 y「using ra­ 32 1.51 0.267 1.55* dioactive ammonium bromide proceed in the nuclear reac­ 32 1.51 0.534 2.30* tor, TRIGA-III, the Korea Advanced Energy Research 32 1.51 1.07 5.90* 1.51 2.14 8.74* Institute. 32 14.6* A small quantity of red phosphorus was added to carbon 32 1.51 3.92 26 0,587 0.261 0.0780* tetrachloride, to which liquid bromine was added 이 °wly 26 0.587 0.521 0.262후 while stirring.
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