The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Walden inversion. XIII. The influence of substituting groups on optical rotation in the series of disubstituted acetic acids》. Authors are Levene, P. A.; Mikeska, L. A..The article about the compound:1-Iodo-2-methylbutanecas:616-14-8,SMILESS:CCC(CI)C).HPLC of Formula: 616-14-8. Through the article, more information about this compound (cas:616-14-8) is conveyed.
cf. C. A. 22, 1953. The conclusion that in the aliphatic series the carbinols and the structurally related halides rotate in opposite directions is substantiated by the study of a series of aliphatic substances derived from disubstituted acetic acids or their corresponding carbinols. Primary halides rotate in the opposite direction to the primary alcs. from which they were derived, while in passing from the corresponding thio to the sulfo derivative the change in rotation is in the same direction, though without change of sign. A decided uniformity was found in the effect on optical rotation of various substitutions of the CO2H group or of the alc. group of the corresponding carbinols, depending upon the position of the subsituting group in the polarity series, C = N > CO2Et > CO2H > CONH2 > COCl > CH2SO3H > CH2X > CH2SH > CH2OH > CH2NH2. The order in this series corresponds with the order of the same groups in polarity series determined by other methods. This relationship holds only for aliphatic substances containing only 1 asym. C atom and only 1 polar group. Active primary amyl alc. was halogenated without marked racemization, while in the rest of the series conversion to the halide from the carbinol by SOCl2, PCl5, HBr, HI, etc., as well as from the amine by NOCl2, led to complete racemization. Optically active halides were obtained in the latter case by the action of NOBr. d-Propylmethylacetic acid, [α]D25 5.58° (Et2O), with SOCl2 gave the d-chloride (I), b15 45-8°; [α]D25 4.06°. I, [α]D25 3.94° (Et2O), with concentrated aqueous NH4OH gave the d-amide, m. 78° (from H2O), [α]D25 5.79° (75% alc.). l-Amide, [α]D25-5.79° (75% alc.), distilled with P2O6 gave l-propylmethylacetonitrile (II), b2 30-2°, [α]D25-13.77°. II with Na-alc. gave d-2-propyl-2-methylethylamine (III), b4 28-30°, [α]D25 3.84°, whose HCl salt had [α]D25 1.51° (50% alc.), l-Propylmethylacetic acid, [α]D25-7.08° (Et2O), with HCl gas in alc. gave the Et ester, b4 78-80°, [α]D25-7.91°. d-Acid Et ester, [α]D25 5.67° (Et2O), with Na-alc. gave l-2-propyl-2-methylethanol (IV), b. 147-7.5°, [α]D25-1.23°. IV with PCl5 or NOCl gave dl-2-propyl-2-methylethyl chloride, b. 110-20°. III with NOBr gave l-2-propyl-2-methylethyl bromide, b10 55-65°, [α]D25-0.94° (Et2O). I with KHS gave d-propylmethylthiolacetic acid, b23 71-2°, [α]D25 7.49°. d-Butylmethylacetic acid (V), [α]D25 5.42° (Et2O), with SOCl2 gave the acid chloride (VI), b9 45-8°, [α]D25 5.06°. VI with NH4OH gave the amide (VII), m. 66° (from H2O), [α]D25 3.86° (75% alc.). VII distilled with P2O5 gave the nitrile (VIII), b9 43-50°, [α]D25 9.40°. In another experiment an amide, [α]D25-11.44°, gave a nitrile, [α]D25-27.09° (Et2O). VIII with Na-alc. gave l-2-butyl-2-methylethylamine, b15 49-54°, [α]D25-3.52° (Et2O), whose HCl salt had [α]D25-2.41° (H2O). V with HCl gas and alc. gave an Et ester, b9 58-62°, [α]D25 6.84°, which with Na-alc. gave d-2-butyl-2-methylethanol, b15 71-2°, [α]D25 2.47° (Et2O). d-Heptylmethylacetic acid (IX), b4 145-7°, [α]D25, whose Na salt, [α]D25 0.84° (H2O), was treated with SOCl2, yielding the acid chloride (X), b1 73-4°, [α]D25 4.89°. X with NH4OH gave the amide (XI), m. 78° (from 50% alc.), [α]D25 7.07° (95% alc.), XI with P2O5 gave the nitrile (XII), b7 85-94°, [α]D25 13.61°. XII with Na-alc. gave 1-2-heptyl-2-methylethylamine (XIII), b24, 103-5°, [α]D25-3.38°, whose HBr salt had [°]D25-4.61° (75% alc.), In another experiment an amine, [α]D25 6.05° (Et2O), was obtained from a nitrile, [α]D25 -15.10° (Et2O). An amine, [α]D25 6.05° (Et2O), was obtained from a HBr salt, [α]D25 5.91°. XIII with HBr (fuming) and NaNO2 gave d-2-heptyl-2-methylethyl bromide, b1 80-5°, [α]D25 2.18° (Et2O). l-Heptylmethylacetic acid, [α]D26 -8.72° (Et2O), with HCl gas and alc. gave the Et ester, b17 122-4°, [α]D25 -8.60°, which with Na-alc, gave d-2-heptyl-2-methylethanol, b0.4 80-2°, [α]D25 3.64°. d-Decylmethylacetic acid, b1 153°, [α]D25 8.47°, showed no rotation when neutralized with NaOH. l-Decylmethylacetic acid (XIV), [α]D25 -6.38° (Et2O), with SOCl2 gave the acid chloride (XV), b0.5 118-25°, [α]D25 -3.5°, which was hydrolyzed, yielding an acid, [α]D25 -5.78° (Et2O). XV with NH4OH gave the amide, m. 77° (from 50% alc.), [α]D25 -3.01° (95% alc.), which with P2O5 gave the nitrile, b0.5 108-10°, [α]D25 -10.87° (Et2O), which with Na-alc. gave d-2-decyl-2-methylethylamine (XVI), [α]D25 4.18°, whose HCl salt, m. 105-18°, [α]D25 3.17° (H2O). XIV with HCl gas and alc. gave an Et ester, b1 141°, [α]D25 -6.48°, which with Na-alc. gave l-2-decyl-2-methylethanol, b1.4 105°, [α]D25 2.34°, XVI with NOBr gave l-2-decyl-2-methylethyl bromide, b0.02 87-90°, [α]D25 -0.39. Primary l-amyl alc., [α]D25 -4.73° (Et2O), with HI gave d-2-ethyl-2-methylethyl iodide, b12 47-50°, [α]D25 3.92° (Et2O), which with KHS gave d-2-ethyl-2-methylethanethiol, b. 116-7°, [α]D25 2.99°. In another experiment an iodide, [α]D25 5.27° (Et2O), gave a mercaptan, [α]D25 6.92°, which with Ba(MnO4)2 gave d-2-ethyl-2-methylethanesulfonic acid, whose Ba salt had [α]D25 5.09° (H2O). A table of mol. rotations of the various derivatives, which do not necessarily agree with the exptl. figures, is appended. These values were calculated on the basis of the parent substance of the highest rotation. There is also a table of d.
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Reference:
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