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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
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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.
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
Page 3
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
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
Page 4
FT
-IR
sp
ectr
um
of
the
sulf
ated
tit
ania
nan
opar
ticl
es
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Page 5
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.
.
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Page 6
1 H N
MR
sp
ectr
um
of
N-p
hen
ylp
rop
ion
amid
e(1i
)
H N
O
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Page 7
13
C N
MR
sp
ectr
um
of
N-p
hen
ylp
rop
ion
amid
e(1i
)
H N
O
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
Page 8
DE
PT
135
spec
tru
m o
f N
-phe
nyl
pro
pio
nam
ide(
1i)
H N
O
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Page 9
1 H N
MR
sp
ectr
um
of
N-p
-tol
ylb
enza
mid
e
HN O
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
Page 10
13C
NM
R s
pec
tru
m o
f N
-p-t
olyl
ben
zam
ide
HN O
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Page 11
1 H N
MR
sp
ectr
um
of
N-m
-tol
ylb
enza
mid
e (3
a)
N H
O
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
Page 12
13C
NM
R s
pec
tru
m o
f N
-m-t
olyl
ben
zam
ide
(3a)
N H
O
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Page 13
1 H N
MR
sp
ectr
um
of
2-p
hen
oxy-
N-m
-tol
ylac
etam
ide
(3c)
HNO
O
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
Page 14
HNO
O
13
C N
MR
sp
ectr
um
of
2-p
hen
oxy-
N-m
-tol
ylac
etam
ide
(3c)
H
NOO
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
Page 15
HNO
O
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
Page 16
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
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