the catalytic activity of titania nanostructures in the ... · the catalytic activity of titania...

The catalytic activity of titania nanostructures in the synthesis of

amides under solvent-free conditions

Sangaraiah Nagarajana, Park Ranb, Poovan Shanmugavelana, Murugan Sathishkumara, Alagusundaram Ponnuswamy*a, Kee Suk Nahm*b, and G. Gnana kumar*c

a Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Tamilnadu 625 021, India.

Email: [email protected]; Tel: +91 9600868323 b Specialized Graduate School of Hydrogen and Fuel Cell Engineering, Chonbuk National University, Jeonju 561-756, Republic

of Korea. Email: [email protected]; Fax: +82 63 270 2306 c Department of Physical Chemistry, School of Chemistry, Madurai Kamaraj University, Tamilnadu 625021, India.

Email: [email protected]; Tel: +91 9585752997

Supporting Information

Electronic Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012

General Experimental section

All chemicals and solvents were of commercially high purity grade purchased from Acros organics

Synthesis Pvt. Ltd. and Sigma-Aldrich Ltd, India. Melting points were obtained on electro-thermal

apparatus and are uncorrected. Conventional transmission electron micrographs were recorded on JEOL

JEM-2010 transmission electron microscope equipped with an energy-dispersive X-ray spectroscopy

(EDX). X-ray diffraction patterns of the prepared materials were characterized by using a (D-Max-3A,

Rigaku XRD) diffractometer. FT-IR spectrum of the sulfated titania nanotubes was recorded between

400-4000 cm-1 transmitance mode using Jasco FT-IR spectrophotometer. Textural properties of the

prepared materials were characterized by using BET surface area analyzer BELSORP. Thermal behavior

of the prepared nanostructured materials was examined on a Perkin-Elmer (Wellesley, MA) instrument

under a nitrogen atmosphere at a heating rate of 20 °C/min from 30 to 800 °C. 1H NMR and 13C NMR

spectra were recorded in CDCl3 on Bruker Avance 300 MHz spectrometer and the chemical shifts are

reported as δ values in parts per million (ppm) relative to tetramethylsilane, with J values in Hertz. The

splitting patterns in 1H NMR spectra are reported as follows: s = singlet; d = doublet; t = triplet; q =

quartet; m = multiplet. 13C NMR data are reported with the solvent peak (CDCl3 = 77.0) as the internal

standard. The spectral data of all known compounds are consistent with those reported previously.


CO

PIE

S O

F F

T-I

R, 1 H

AN

D 13

C N

MR

SP

EC

TR

A O

F R

EP

RE

SE

NT

AT

IVE

AM

IDE

S


FT

-IR

sp

ectr

um

of

the

sulf

ated

tit

ania

nan

opar

ticl

es


FT

-IR

sp

ectr

um

of

the

sulf

ated

tit

ania

nan

otu

bes

F

igur

e e

xhib

its i

nfra

red

spec

trum

of

the

sulf

ated

tit

aniu

m o

xide

nan

otub

es a

nd t

he o

btai

ned

peak

s ar

e as

sign

ed a

s fo

llow

s.

Inte

nsiv

e ba

nds

obse

rved

at

3437

and

163

6 cm

−1 a

re

attr

ibut

ed to

the

str

etch

ing

vibr

atio

n of

hyd

roxy

l gro

ups

and

adso

rbed

wat

er m

olec

ules

, res

pect

ivel

y.

The

S=

O s

tret

chin

g of

the

sul

fate

d ti

tani

a na

notu

bes

wer

e fo

und

at 1

052

and

1132

cm

-1 w

hich

rep

rese

nt t

he s

ucce

ssfu

l im

plan

tati

on o

f su

lfon

ic a

cid

moi

etie

s ov

er th

e ti

tani

a na

notu

bes.

Sig

nifi

cant

ban

ds o

bser

ved

in th

e re

gion

400

-100

0 cm

-1, r

epre

sent

s T

i-O

fra

mew

ork

stre

cthi

ng f

requ

enci

es.

.


1 H N

MR

sp

ectr

um

of

N-p

hen

ylp

rop

ion

amid

e(1i

)

H N

O


13

C N

MR

sp

ectr

um

of

N-p

hen

ylp

rop

ion

amid

e(1i

)

H N

O


DE

PT

135

spec

tru

m o

f N

-phe

nyl

pro

pio

nam

ide(

1i)

H N

O


1 H N

MR

sp

ectr

um

of

N-p

-tol

ylb

enza

mid

e

HN O


13C

NM

R s

pec

tru

m o

f N

-p-t

olyl

ben

zam

ide

HN O


1 H N

MR

sp

ectr

um

of

N-m

-tol

ylb

enza

mid

e (3

a)

N H

O


13C

NM

R s

pec

tru

m o

f N

-m-t

olyl

ben

zam

ide

(3a)

N H

O


1 H N

MR

sp

ectr

um

of

2-p

hen

oxy-

N-m

-tol

ylac

etam

ide

(3c)

HNO

O


HNO

O

13

C N

MR

sp

ectr

um

of

2-p

hen

oxy-

N-m

-tol

ylac

etam

ide

(3c)

H

NOO


HNO

O


1 H N

MR

sp

ectr

um

of

2-p

hen

oxy-

N-p

-tol

ylac

etam

ide

(2c)

13C

NM

R s

pec

tru

m o

f 2-

phe

nox

y-N

-p-t

olyl

acet

amid

e (2

c)

HNO

O


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