P-Iodoaniline

Into a 1-litre beaker, provided with a mechanical stirrer, place 36 - 8 g. (36 ml.) of aniline, 50 g. of sodium bicarbonate and 350 ml. of water cool to 12-15° by the addition of a little crushed ice. Stir the mixture, and introduce 85 g. of powdered, resublimed iodine in portions of 5-6 g, at intervals of 2-3 minutes so that all the iodine is added during 30 minutes. Continue stirring for 20-30 minutes, by which time the colour of the free iodine in the solution has practically disappeared and the reaction is complete. Filter the crude p-iodoaniline with suction on a Buchner funnel, drain as completely as possible, and dry it in the air. Save the filtrate for the recovery of the iodine (1). Place the crude product in a 750 ml. round-bottomed flask fitted with a reflux double surface condenser add 325 ml. of light petroleum, b.p. 60-80°, and heat in a water bath maintained at 75-80°. Shake the flask frequently and after about 15 minutes, slowly decant the clear hot solution into a beaker set in a freezing mixture of ice and salt, and stir constantly. The p-iodoaniline crystallises almost immediately in almost colourless needles filter and dry the crystals in the air. Return the filtrate to the flask for use in a second extraction as before (2). The yield of p-iodoaniline, m.p. 62-63°, is 60 g. 

Two extractions usually sufiSce, but if much organic material remains, a third extraction should be made. If the p-iodoaniline from the second and third extractions is coloured, it should be refluxed for a short period in light petroleum solution with a little decolourising carbon and filtered through a hot water funnel (CA U TION inflammable). 

FIGURE 3.4 Schematic drawing of the complex of P-cyclodextrin and p-iodoaniline. ... 

C3gHg()03Q CgHglN 3 H20 Cyclomaltohexaose -p-iodoaniline, trihydrate CDEXIA, 01, 37 407... 

Iodine, detection of, 1041, 1042, 1043, 1045 recovery of, 647 Iodine monochloride, 974 5-Iodo-2-ammotoluene, 647 p-Iodoaniline, 647 Iodobenzene, 533, 538, 591, 598 Iodobenzene diacetate, 541 Iodobenzene dichloride, 534, 541 o-Iodobenzoic acid, 760... 

C3eH6o03o-CeH4IN-3H20 a-Cyclohexaamylose p-iodoaniline trihydrate73... 

Boyd and coworkers583 also labelled lima-bean lectin with 131I (indirectly, by coupling of [131I]-p-iodoaniline to protein by diazotization)584 and visible dyes,584,585 and quantitated the binding to type A erythrocytes. 

Fig. 10-3 shows the obtained S-dependence of AR(B) for the reaction of thionine with p-iodoaniline in methanol. As clearly seen from this figure, the AR value decreases with increasing B from 0 to 0.414 T. Using other donors, he also measured the AR(B) values for their reactions. The obtained (0.414 T) values are plotted against

Fig. 10-3. Relative magnetic field effect AR (cf. Eq. (10-9)) as a function of magnetic field for the triplet exciplex thionine/p-iodoaniline. Circles with error bars represent the experimental results obtained in Ref. [3]. Lines are calculated with an equation similar to Eq. (10-17) and the different values for p indicated in the diagram. (Reproduced from Ref. [4a] by permission from The Royal Society of Chemistry)...

Fig. 10-6 shows the observed AR(B) values in the reaction from the triplet exciplex (thionine/p-iodoaniline) and the theoretical prediction of AR(B) with the different values for AR(B— cc). As clearly seen from this figure, the MFE of this reaction is saturated at about 2... 

Cinnamoyl- 6-CD (6-CiO-/3-CD) was sparingly soluble in water, although most 6-substituted 6-CDs are soluble. However, 6-CiO-/3-CD was solubilized in water on the addition of adamantane carboxylic acid or p-iodoaniline which could be included in a 6-CD cavity. These results suggest that 6-CiO-/l-CD formed supramolecular polymers in the solid state, as shown in the proposed structure in Fig. 17. The X-ray powder pattern of 6-CiO-/l-CD was similar to that of the complex between p-CD and ethyl cinnamate, in which /3-CDs formed a layer structure. The crystal structure of 6-aminocinnamoyl-/3-CD (6-aminoCiO-/l-CD) is shown in Fig. 12 and we discussed the relationship between crystal packing and the substituent group in Sect. 2.8. 

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