Chloromethyl Research Articles

Immobilization of formaldehyde dehydrogenase in tailored siliceous mesostructured cellular foams and evaluation of its activity for conversion of formate to formaldehyde

Formaldehyde dehydrogenase (FaldDH) is used as a catalyst to reduce formate to formaldehyde in a cascade reaction to convert CO2 to methanol. This enzyme, however, has low activity and is sensitive to substrate/product concentration and pH. To improve the performance of FaldDH, it can be immobilized through physical adsorption in siliceous mesostructured cellular foams (MCF), which physical properties are suitable for the immobilization of large molecules as FaldDH (molecular size of 8.6 × 8.6 × 19 nm). In this work two MCF materials were synthesized: MCF1 with a pore size of 26.8 nm and window size of 10.5 nm; and MCF2 with a pore size of 32.9 nm and window size of 13.0 nm. The surfaces of the materials were functionalized with octyl, mercaptopropyl or chloromethyl groups. FaldDH was successfully immobilized inside all the materials, yielding enzyme loadings of about 300 mg g‐1 in MCF1 and more than 750 mg g−1 in MCF2. However, the enzyme was inactive upon immobilization on MCF1, whereas on MCF2 the enzyme retained its catalytic activity presumably owing to the larger pores of this material and the need for the enzyme to undergo configurational changes during the reaction. Using MCF2 functionalized with mercaptopropyl groups the activity of FaldDH was enhanced beyond that of the free enzyme. Additionally, low leakage of the enzyme from the MCF2 was observed during the reactions. Thus, tailored MCF is a highly attractive material for employment of the FaldDH enzyme.

Reaction of (chloromethyl)trichlorosilane with 2,2-dimethylpropane-1,3-diol

(Chloromethyl)trichlorosilane reacts with 2,2-dimethylpropane-1,3-diol to produce α-carbofunctional heterocycles, 2-chloro-2-(chloromethyl)-5,5-dimethyl-1,3,2-dioxasilinane and 2,8-dichloro-2,8-bis(chloromethyl)-5,5,11,11-tetramethyl-1,3,7,9-tetraoxa-2,8-disilacyclododecane. The synthesized macroheterocycle is the first structurally characterized 1,3,7,9-tetraoxa-2,8-disilacyclododecane derivative.

Investigation of adsorption mechanism of Fe, Cu, and Zn ions in extraction and preconcentration process on synthesized graphene oxide using an indole derivative

3-(chloro(2-methyl-1H-indol-3-yl)methyl)-2-methyl-1H-indole (MIMI) was chosen for separation and preconcentration of iron (III), copper (II), and zinc by solid-phase extraction (SPE). Ion–MIMI chelates are adsorbed onto synthesized graphene oxide (GO) as adsorbent, eluted with HNO3 and determined by flame atomic absorption spectrometry (FAAS). The adsorption mechanism of titled metal complexes on GO was investigated by using computational chemistry approach based on PM7 semi-empirical potential energy surface. The influences of analytical parameters were investigated. The interference effect of common cations tested did not interfere with the recovery of understudied ions. The preconcentration factor of 312.5 and the detection limits of 0.62, 0.28, and 0.05 ng mL−1 for iron (III), copper (II), and zinc, respectively, were obtained. The developed SPE method was successfully utilized for the determination of trace metal ions in different certified reference materials and real samples (including water, cheese, honey, tomato, leaves of spinach, and milk) by FAAS.

Exploring the structural landscape by chloro–methyl exchange

Exploring the structural landscape by chloro–methyl exchange

Aerogels from Chloromethyltrimethoxysilane and Their Functionalizations.

Reactions of chloromethyltrimethoxysilane (CMTMS) and its derived colloidal network polychloromethylsilsesquioxane (PCMSQ) have been investigated to extend the material design strategy toward functionalized and mechanically reinforced aerogels. In a carefully designed sol-gel system, CMTMS has afforded transparent aerogels in the presence of cationic surfactant. The surface chloromethyl groups with polarity and reactivity are shown to be useful for supporting nanostructures, with photoluminescent carbon dots (C-dots) prepared from polyethylenimine and citric acid as an example. Furthermore, since nucleophilic substitution (SN2) reactions on the surface chloromethyl groups are found to control the equilibrium of formation/dissociation of siloxane bonds, a new gelation strategy triggered by SN2 reactions in sol-gel has been developed. In the presence of nucleophilic organic species such as polyamines, a hybrid network consisting of PCMSQ cross-linked with a polyamine nucleophile can be prepared to enhance mechanical properties of aerogel.

The Ultraviolet-Induced Functionalization of Multi-Walled Carbon Nanotubes with Polymer Radicals Generated from Polyvinyl Benzoate Derivatives

In order to develop a novel technique for the fabrication of hybrid materials containing polymers and nanocarbons, we examined the surface modification of pristine multi-walled carbon nanotubes (MWCNTs) with benzyl-type polymer side chain radicals generated through photolysis of 4-(chloromethyl)benzoate moieties. The polymer with a 4-(chloromethyl)benzoate side chain was prepared by the esterification of polyvinyl alcohol (PVA) with corresponding acid chloride. The synthesized polymer and MWCNTs were mixed in N-methylpyrrolidone and irradiated with ultraviolet (UV) light. Structural changes of the polymer and MWCNTs were observed by means of X-ray photoelectron spectroscopy (XPS) and Raman spectroscopy. The XPS results revealed that scission of the C–Cl bonds of the chloromethyl groups and benzyl-type radical formation occurred. The incremental surface defects of the MWCNTs caused by UV irradiation were confirmed by means of Raman spectroscopy. These results support the covalent bond formation between the polymer side chain and MWCNT sidewalls by radical addition reaction. The photothermal conversion characteristics of the prepared materials were also evaluated.

Synthesis of poly(acrylonitrile‐co‐divinylbenzene‐co‐vinylbenzyl chloride)‐derived hypercrosslinked polymer microspheres and a preliminary evaluation of their potential for the solid‐phase capture of pharmaceuticals

ABSTRACTPoly[acrylonitrile (AN)‐co‐divinylbenzene (DVB)‐co‐vinylbenzyl chloride (VBC)] terpolymers were synthesized by precipitation polymerization in the form of porous polymer microspheres. The poly(AN‐co‐DVB‐co‐VBC) polymers were then hypercrosslinked, via a Friedel‐Crafts reaction with FeCl3 in nitrobenzene, to provide a significant uplift in the specific surface areas of the polymers. FTIR spectra of the hypercrosslinked poly(AN‐co‐DVB‐co‐VBC)s showed that the chloromethyl groups derived from VBC were consumed by the Friedel‐Crafts reactions, which was consistent with successful hypercrosslinking. Hypercrosslinking installed a number of new, small pores into the polymers, as evidenced by a dramatic increase in the specific surface areas upon hypercrosslinking (from ∼530 to 1080 m2 g−1). The hypercrosslinked polymers are very interesting for a range of applications, not least of all for solid‐phase extraction (SPE) work, where the convenient physical form of the polymers (beaded format), their low mean particle diameters, and narrow particle size distributions, as well as their high specific surface areas and polar character (arising from the AN residues), make them attractive candidates as SPE sorbents. In this regard, in a preliminary study one of the hypercrosslinked polymers was utilized as an SPE sorbent for the capture of the polar pharmaceutical diclofenac from a polar environment. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 45677.

Reaction of diphenylphosphinoylallene derivatives of cytisine

Diphenylphosphinoylallenes containing a ClCH2 group were synthesized, and their reaction with cytisine was studied. It was shown that the reaction involves exclusives as nucleophilic substitution of chlorine in the chloromethyl group. The synthesized conjugates of cytisine with diphenylphosphinoylallene derivatives are of interest as potential agonists of nicotinic acetylcholine neuroreceptors (nAChRs).

Reaction of transsilylation of N-methyl-N-trimethylsilylacetamide with silanes ClCH2SiR1R2Cl

The reaction of N-methyl-N-trimethylsilylacetamide with silanes ClCH2SiR1R2Cl (R1, R2 = H, Me; H, Ph; Ph2) leads to the formation of (O→Si) chelate compounds with pentacoordinate silicon: N-[chloro(methyl)-silyl]methyl-, N-[chloro(phenyl)silyl]methyl-, and N-[chloro(diphenyl)silyl]methyl-N-methylacetamides. From the data of multinuclear NMR spectroscopy, the intermediates of the reaction of N-methyl-N-trimethylsilylacetamide with ClCH2SiPhHCl and ClCH2SiPh2Cl are stable in CDCl3 solution at room temperature during several days and slowly rearrange to the final (O–Si) chelate compounds.

Functional polylactide by cationic ring-opening copolymerization of lactide with epoxides

Sequential and simultaneous cationic copolymerizations of lactide with commercial functional epoxides: allyl glycidyl ether, glycidyl propargyl ether, and epichlorohydrin, catalyzed by a protic acid in a one-pot process were studied. Block and gradient polylactide-based medium-molecular-weight copolymers with several alkene, alkyne, or chloromethyl groups at one chain end or with gradient distribution along the polymer chain were successfully synthesized, as proven by 1H NMR, SEC, and MALDI TOF analyses. Functional polylactides were further subjected to thiol-ene addition, cycloaddition of azide, or reaction with tertiary amine, respectively, to demonstrate the reactivity of the introduced functional groups.

Consecutive reaction of 1-chlorovinyl p-tolyl sulfoxides with [chloro(p-tolylsulfinyl)methyl]lithium leading to the formation of multi-functionalized methylenecyclopropanes

The reaction of 1-chlorovinyl p-tolyl sulfoxides with excess [chloro(p-tolylsulfinyl)methyl]lithium gave methylenecyclopropanes consisting of a chloro(p-tolylsulfinyl)methylene moiety and a (p-tolylsulfinyl)cyclopropylidene moiety. Treating the methylenecyclopropanes with butyllithium resulted in the formation of conjugated enynes.

UNUSUAL WAY OF REACTION OF 3-AMINO-4-(5-CHLOROMETHYL-1,2,4-OXADIAZOLE-3-YL)-FURAZAN WITH HYDRAZINE

The results of our study of the pathways of selective reactivity of 3-amino-4-(5-chloromethyl-1,2,4-oxadiazole-3-yl)furazan versus 5-unsubstituted or 5-methyl and 5-trifluoromethyl substituted 4-(5R-1,2,4-oxadiazole-3-yl)furazans (R = H, Me, CF3) towards the action of hydrazine are discussed. If the reductive opening of 1,2,4-oxadiazole ring in unsubstituted at the С-5 atom (1,2,4-oxadiazol-3-yl)furazan derivatives under the treatment with hydrazine can be used as a method for the preparation of a range of amidrazones of 4-R-furazan-3-carboxylic acid. 3-amino-4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)furazan with hydrazine gives amidoxime of 4-aminofurazan-3-carboxylic acid. 3-amino-4-(5-methyl-1,2,4-oxadiazol-3-yl) furazan is inert to the action of hydrazine, on the contrary the reaction of 3-amino-4-(5-chloromethyl-1,2,4-oxadiazole-3-yl)furazan with hydrazine leads to oxidation of chloromethyl group of titled compound to the carbonyl one. In this case the product of reaction of 3-amino-4-(5-chloromethyl-1,2,4-oxadiazole-3-yl)furazan with hydrazine was isolated in a form of corresponding hydrazonomethyl derivative notably as 3-amino-4-(5-hydrazonomethyl-1,2,4-oxadiazole-3-yl)furazan. A possible reaction mechanism for the formation of hydrazonomethyl group by oxidation reaction of chloromethyl group by hydrazine is proposed. 3-Amino-4-(5-hydrazonomethyl-1,2,4-oxadiazol-3-yl)furazan undergoes a transhydrazination reaction with semicarbazide and thiosemicarbazide. But our attempts to its hydrolysis for the purpose to obtain free aldehyde were unsuccessful. Thus, hydrolysis of hydrazonomethyl derivative in acetic acid in the presence of catalytic amount of sulfuric acid results in azine – N,N'-bis(3-(4-aminofurazan-3-yl)-1,2,4-oxadiazol-5-ylmethylyden)hydrazine – precipitation, long-duration boiling in hydrochloric acid leads to Kishner-Wolff reduction of the carbonyl group to 3-amino-4-(5-methyl-1,2,4-oxadiazol-3-yl)furazan, and hydrolysis in alkaline medium leads to 1,2,4-oxadiazole ring opening to amidoxime of 4-aminofurazan-3-carboxylic acid. Synthesis of 3-amino-4-(5-chloromethyl-1,2,4-oxadiazole-3-yl)furazan (R = CH2Cl) was carried out by condensation of amidoxime of 4-aminofurazan-3-carboxylic acid with an excess of chloroacetyl chloride in toluene at elevated temperature. The reaction proceeds through formation of intermediate product – 3-chloromethylamino-4-(5-chloromethyl-1,2,4-oxadiazol-3-yl)furazan. Removing of N-chloroacetyl group in such obtained intermediate was performed by hydrolysis in acidic media. One-pot synthesis without the need for isolation and purification of intermediate is allowed. The structures of obtained compounds were proved by modern methods of physical-chemical analysis (1H, 13C NMR, IR and MS spectroscopy).Forcitation:Stepanova E.V., Stepanov A.I. Unusual way of reaction of 3-amino-4-(5-chloromethyl-1,2,4-oxadiazole-3-yl)furazan with hydrazine. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2017. V. 60. N 4. P. 26-32.

Synthesis and bioactivities of Phenazine-1-carboxylic acid derivatives based on the modification of PCA carboxyl group

Phenazine-1-carboxylic acid (PCA) as a natural product widely exists in microbial metabolites of Pseudomonads and Streptomycetes and has been registered for the fungicide against rice sheath blight in China. To find higher fungicidal activities compounds and study the effects on fungicidal activities after changing the carboxyl group of PCA, we synthesized a series of PCA derivatives by modifying the carboxyl group of PCA and their structures were confirmed by 1H NMR and HRMS. Most compounds exhibited significant fungicidal activities in vitro. In particular, compound 6 exhibited inhibition effect against Rhizoctonia solani with EC50 values of 4.35mg/L and compound 3b exhibited effect against Fusarium graminearum with EC50 values of 8.30mg/L, compared to the positive control PCA with its EC50 values of 7.88mg/L (Rhizoctonia solani) and 127.28mg/L (Fusarium graminearum), respectively. The results indicated that the carboxyl group of PCA could be modified to be amide group, acylhydrazine group, ester group, methyl, hydroxymethyl, chloromethyl and ether group etc. And appropriate modifications on carboxyl group of PCA were useful to extend the fungicidal scope.

Inherently fluorescent polystyrene microspheres for coating, sensing and cellular imaging

Commercially available polystyrene (PS) fluorescent microspheres are widely used in biological field for tracing, in vivo imaging and calibration of flow cytometry, among other applications. However, these particles do suffer from some drawbacks such as the leakage and photobleaching of organic dyes within them. In the present study, inherently fluorescent properties of PS based microspheres have been explored for the first time. Here we find that a simple chloromethylation reaction endows the polystyrene particles with inherent fluorescence without any subsequent conjugation of an external fluorophore. A possible mechanism for fluorescence is elucidated by synthesizing and investigating p-ethylbenzyl chloride, a compound with similar structure. Significantly, no photobleaching or leaking issues were observed owing to the stable structure of the microspheres. Chloromethylated PS (CMPS) microspheres can keep their perpetual blue fluorescence even in dry powder state making them attractive as a potential coating material. Furthermore, the chloromethyl groups on CMPS microspheres make them very convenient for further functionalization. Poly(ethylene glycol) (PEG) grafted microspheres showed good biocompatibility and negligible cytotoxicity, and could be used to image intracellular Fe3+ due to the selective fluorescence quenching effect of aqueous Fe3+ in cytoplasm.

4-(2-chloroacetamido) Benzoic Acid Derivatives as Local Anesthetic Agents: Design, Synthesis, and Characterization

Local anesthetic activity was investigated with an assumed hypothesis that the essential alkyl substituted nitrogen having strong ionization characteristics (pKa in basic side) generally found in local anesthetics can be replaced by amide nitrogen, having chloro methyl group attached to the carbonyl carbon of amide. In this type of arrangement, the inductive effect exerted by chlorine provided enough ionization character to amide nitrogen. Eight esters, ten amides and one imidazole derivatives of 4-(2-chloroacetamido) benzoic acid were synthesized by Fischer’s esterification, Schotten-Baumann and substitution reactions. The synthesized derivatives (A1–A18 and A.im) were characterized by various instrumental techniques.ACD Lab Suite® was used to determine various physiochemical properties of synthesized molecules. Initially, infiltration local anesthetic activity was determined by Bianchi’s method. Five compounds (A1, A2, A4, A10, and A.im) showed promising local anesthetic activity, where the comparison was made with lignocaine HCl, thus conforming assumed hypothesis. However, the studied compounds have potency lower than that of lignocaine HCl. Compounds showing promising activity with low toxicity were studied further by in-vivo rat sciatic nerve block method using increasing doses. A.im was studied for topological similarity with lignocaine HCl where it showed good local anesthetic activity and was relatively very less toxicity. The reduced toxicity of these molecules may be attributed due to the carbonyl chloro methyl side chain. Further structural advancement may be done by researchers to increase the potency of these compounds since they are relatively less toxic than lignocaine.

Synthesis and Properties of Partially Fluorinated Anion Exchange Membranes Containing Ammonium-Functionalized Fluorenyl Groups

Anion exchange membrane fuel cells (AEMFCs) are one of the promising energy conversion devices because of their high efficiency and possible use of non-precious metal catalysts. However, the existing anion exchange membranes, main component of AEMFCs, do not show sufficient ion conductivity and stability. In this study, we report a novel series of AEMs composed of perfluoroalyl chains and ammonium-functionalized fluorenyl groups (Fig. 1). The perfluoroalkyl groups are expected to provide chemical stability as well as flexible membrane forming capability, while the ammonium-functionalized fluorenyl groups contain high ionic density for high ion conductivity. We have investigated in details synthetic procedure, structure, and properties of the title AEMs. The hydrophobic monomer containing perfluroaklyl groups was synthesized by Cu-catalyzed Ullmann coupling reaction, and fluorenyl-containing monomers were synthesized by Sandmeyer reaction. Precursor polymers were synthesized by Ni-mediated Ullman coupling reaction. Then, chloromethyl groups were introduced onto the precursor polymers by Friedel-Crafts reaction. The chloromethyl groups were quarternized with trimethyl amine by Menshutkin reaction. It is known that the chloromethylation reaction often accompanies with unfavorable side reactions such as cross-linking. By carefully optimizing the Friedel-Crafts reaction conditions, we have successfully controlled the degree of chloromethylation. In fact, the number and the position of chloromethyl groups substituted on fluorenyl groups were controllable. The chloromethylated precursors were soluble in organic solvent and the solutions were cast to thin films. The ion exchange capacities obtained by titration were lower than calculate from DC. The difference of IEC value was increased with increase of DC. It is suggest that when ionic group density becomes higher, there is an ammonium group which is not functioning as ionic groups by their steric hindrance. The quaternized polymer membranes exhibited high hydroxide ion conductivity and the maximum conductivity was 29 mS/cm in water at 80 °C for the membrane with IEC = 1.6 meq/g. It was found that meta-linked polymers in the hydrophilic component showed slightly higher ion conductivity than that of para-linked polymers. Other properties such as morphologies and stabilities will also be reported. Acknowledgement This work was partly supported by Japanese Science and Technology Agency (JST), CREST. References 1) Manai Shimada, Shigefumi Shimada, Junpei Miyake, Makoto Uchida, Kenji Miyatake, J. Polym. Sci., A: Polym. Chem., 2015, 7,935-944. 2) Hideaki Ono, Junpei Miyake, Shigehumi Shimada, Makoto Uchida and Kenji Miyatake, J. Mater. Chem. A, 2015, 3, 21779–21788. Figure 1

A convenient synthesis of 1-aralkyl-4-benzylpiperazine derivatives

An efficient two-step route was developed for the synthesis of 1-aralkyl-4-benzylpiperazine derivatives by a Blanc reaction and alkylation. The key intermediate, N-benzylpiperazine, was prepared in an excellent yield by direct benzylation of commercially available piperazine under metal-free conditions.

Anion Exchange Membrane Separators Based on Polystyrene-Block-Poly(ethylene-ran-butylene)-Block-Polystyrene Triblock Copolymers

There is a growing interest in using anion exchange membranes (AEMs) as separators in alkaline membrane fuel cells (AMFCs) and in other energy conversion and storage systems such as redox flow batteries (RFBs), alkaline water electrolyzers (AWEs) and reverse electrodialysis (RED) cells. The most commonly used cation in AEMs is the benzyl trimethylammonium cation. It is easy to synthesize due to the basicity of the trimethylamine, results in relatively large ion exchange capacities (IECs), and the resulting AEMs have good ionic conductivities. AEMs based on the benzyl trimethylammonium cation are good candidates for separators in redox flow batteries. However, it had been shown that the quaternary-ammonium-based AEMs are sensitive towards Hofmann elimination and direct nucleophilic elimination reactions under alkaline conditions, which impedes their use in AMFCs and AWEs. To solve the alkaline stability problem encountered by quaternary ammonium cations, researchers have investigated cations without alpha hydrogens to avoid degradation through ylide formation. Gu and Yan (1) first synthesized a polysulfone based ionomer containing the benzyl tris-(2,4,6-trimethoxyphenyl) phosphonium (TTMP+) cation and they found it had an outstanding stability under alkaline conditions. In our lab, we attempted to attach TTMP to polyphenylene oxide (PPO) and other polymer backbones to make alkaline stable AEMs, but the resultant AEMs were extremely brittle. Therefore, we have devoted attention to studying more robust backbones.Polystyrene-block-poly-(ethylene-ran-butylene)-block-polystyrene (SEBS) is a chemically stable and elastomeric triblock copolymer, which deforms elastically to accommodate bulky cations (TTMP+) without becoming too brittle. There have been several attempts to make SEBS-based AEM by chloromethylation, however, the degree of functionalization (DF) obtained were relatively low due to gelation during the reaction (2, 3). In our work, we have optimized the chloromethylation conditions by selecting the appropriate solvent, temperature and reaction time. The resulting polymers have DFs up to 0.3 (mol of chloromethyl groups per polymer repeat unit). We have been able to synthesize highly robust SEBS-based AEMs containing benzyl trimethyl ammonium (TMA+) and benzyl tris- (2,4,6-trimethoxyphenyl) phosphonium (TTMP+) cations. 1H-NMR spectroscopy, ion exchange capacity and tensile tests were employed to characterize the AEMs. We will report the results obtained.

DMFC Performance of Polymer Electrolyte Membranes Prepared from a Graft-Copolymer Consisting of a Polysulfone Main Chain and Styrene Sulfonic Acid Side Chains

Polymer electrolyte membranes (PEMs) for direct methanol fuel cell (DMFC) applications were prepared from a graft-copolymer (PSF-g-PSSA) consisting of a polysulfone (PSF) main chain and poly(styrene sulfonic acid) (PSSA) side chains with various average distances between side chains (Lav) and side chain lengths (Lsc). The polymers were synthesized by grafting ethyl p-styrenesulfonate (EtSS) on macro-initiators of chloromethylated polysulfone with different contents of chloromethyl (CM) groups, and by changing EtSS content in the copolymers by using atom transfer radical polymerization (ATRP). The DMFC performance tests using membrane electrode assemblis (MEAs) with the three types of the PEMs revealed that: a PSF-g-PSSA PEM (SF-6) prepared from a graft copolymer with short average distances between side chains (Lav) and medium Lsc had higher DMFC performance than PEMs with long Lav and long Lsc or with short Lav and short Lsc. SF-6 had about two times higher PDmax (68.4 mW/cm2) than Nafion® 112 at 30 wt % of methanol concentration. Furthermore, it had 58.2 mW/cm2 of PDmax at 50 wt % of methanol concentration because of it has the highest proton selectivity during DMFC operation of all the PSF-g-PSSA PEMs and Nafion® 112.

Structural, spectroscopic (FT-IR, FT-Raman, NMR) and computational analysis (DOS, NBO, Fukui) of 3,5-dimethylisoxazole and 4-(chloromethyl)-3,5-dimethylisoxazole: A DFT study

The theoretical and computational analysis of two isoxazole derivatives 3,5-dimethylisoxazole and 4-chloromethyl-3,5-dimethylisoxazole were carried out along with some of the experimental evidences. The density functional theory calculations of these compounds were done with DFT/B3LYP/6-31+G(d,p) basis set using Gaussian 09 software. From the DFT calculations, the optimization geometry, vibrational analysis, electronic properties, local reactivity descriptors, natural bond orbitals, and other structural properties of the title compounds were elucidated. The chemical shifts of every C and H atom of the title compounds were calculated using Gauge Independent Atomic orbitals (GIAO) method for both proton and carbon NMR spectra. The molecular electrostatic potential of DMI has been found out and the difference in MEP on addition of chloromethyl group is also discussed. The hyperpolarizability calculations of the investigated molecules shows that the nonlinear optical activity of CDMI is greater when compared to DMI.