Microwave-assisted solvent-free synthesis of some styryl dyes with benzimidazole nucleus

Article abstract of DOI:10.1081/SCC-120038508

A series of styryl dyes: 2-substituted styryl benzimidazole and α-methyl-2-substituted styryl benzimidazole were synthesized under solvent-free microwave irradiation by the condensation of 2-methylbenzimidazole or 2-ethylbenzimidazole with aromatic aldehydes in the presence of Ac ₂O.

Full text of DOI:10.1081/SCC-120038508

This article was downloaded by: [Michigan State University]
On: 04 March 2015, At: 06:59
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer
House, 37-41 Mortimer Street, London W1T 3JH, UK
Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic
Chemistry
Publication details, including instructions for authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
Microwave‐Assisted Solvent‐Free Synthesis of Some
Styryl Dyes with Benzimidazole Nucleus
Lanying Wang a , Xiaogang Zhang a , Fengmei Li a & Zuxun Zhang a
a Department of Chemistry , Northwest University , Shaanxi, Xi'an, 710069, P.R. China
Published online: 17 Aug 2006.
To cite this article: Lanying Wang , Xiaogang Zhang , Fengmei Li & Zuxun Zhang (2004) Microwave‐Assisted Solvent‐Free
Synthesis of Some Styryl Dyes with Benzimidazole Nucleus, Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 34:12, 2245-2252, DOI: 10.1081/SCC-120038508
To link to this article: http://dx.doi.org/10.1081/SCC-120038508
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained
in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no
representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of
the Content. Any opinions and views expressed in this publication are the opinions and views of the authors,
and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied
upon and should be independently verified with primary sources of information. Taylor and Francis shall
not be liable for any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other
liabilities whatsoever or howsoever caused arising directly or indirectly in connection with, in relation to or
arising out of the use of the Content.
This article may be used for research, teaching, and private study purposes. Any substantial or systematic
reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any
form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http://
www.tandfonline.com/page/terms-and-conditions

SYNTHETIC COMMUNICATIONSw
Vol. 34, No. 12, pp. 2245–2252, 2004
Microwave-Assisted Solvent-Free
Synthesis of Some Styryl Dyes
with Benzimidazole Nucleus
*
Lanying Wang, Xiaogang Zhang, Fengmei Li,
and Zuxun Zhang
Department of Chemistry, Northwest University,
Shaanxi, Xi’an, P.R. China
ABSTRACT
A series of styryl dyes: 2-substituted styryl benzimidazole and a-methyl-
2-substituted styryl benzimidazole were synthesized under solvent-free
microwave irradiation by the condensation of 2-methylbenzimidazole
or 2-ethylbenzimidazole with aromatic aldehydes in the presence of Ac2O.
Key Words: Styryl dyes; Microwave irradiation; Ac2O; Benzimidazole
nucleus.
*
Correspondence: Lanying Wang, Department of Chemistry, Northwest University,
Shaanxi, Xi’an, 710069, P.R. China; Fax: þ86-29-88303798; E-mail: wanglany@
nwu.edu.cn.
2245
DOI: 10.1081/SCC-120038508
0039-7911 (Print); 1532-2432 (Online)
www.dekker.com
Copyright # 2004 by Marcel Dekker, Inc.

ORDER
REPRINTS
2246
Wang et al.
INTRODUCTION
Styryl dyes are widely used as sensitizers and other additives in the photo-
graphic industry.[1–4] They are also an important group of biologically active
compounds and have been widely used in pharmaceutical industry.[5] Our
previous efforts have been devoted to develop the synthesis and applications
of cyanine and styryl dyes.[6–9] Classical synthesis of styryl dyes with benzi-
midazole nucleus is often carried out by the reaction of 2-alkylbenzimidazole
and aromatic aldehydes at high temperature.[2,10,11] This preparation has
substantial drawbacks, such as relatively strenuous reaction conditions,
namely, heating reactants for several hours at high temperature and complex-
ity of isolation of the products. Microwave irradiation technique has been used
for the rapid synthesis of a variety of compounds, and microwave-accelerated
solvent-free organic reactions have received special attention in recent
years.[12,13] In this paper, a microwave-assisted preparation of a series of styryl
dyes via condensation of 2-alkylbenzimidazole and a variety of aromatic alde-
hydes without solvent is described in high yield (Sch. 1). The approach
provides an attractive and environmental friendly pathway to several syntheti-
cally useful styryl dyes.
RESULTS AND DISCUSSION
In all cases investigated, we found that the styryl dyes with benzimidazole
nucleus formation reactions proceeded efficiently with high to excellent
yields in short reaction time (Table 1). 2-Substituted styryl benzimidazole
dyes 1a–g were isolated in 87–97% yield within 1–8 min when a mixture
of 10 mmol 2-methylbenzimidazole, 12 mmol aromatic aldehydes and a few
drops of Ac2O was subjected to microwave irradiation at 162–522 watts
under solvent-free conditions. Similarly, a-methyl-2-substituted styryl
benzimidazole dyes 2a–f were also synthesized in good yield (89–93%)
Scheme 1.

ORDER
REPRINTS
Synthesis of Styryl Dyes with Benzimidazole Nucleus
2247
Table 1. The reaction conditions and yields for the synthesis of dyes.
Time
(min)
Power
(W)
Yield
(%)
Time
(min)
Power
(W)
Yield
(%)
Compounds
Compounds
1a
1b
1c
1d
1e
1f
2
3
2
2
3
1
8
324
324
324
162
324
324
522
89
87
97
91
92
95
93
2a
2b
2c
2d
2e
2f
2
3
5
6
4
4
700
252
567
567
567
567
92
95
93
92
89
94
1g
under the present reaction conditions. In the experiment, the products could
be easily purified by recrystallization from the diluted ethyl alcohol. Besides,
excess chemicals in classical synthesis of styryl dyes were avoided or
minimized.
The structure and purity of the prepared styryl dyes 1a–g, 2a–f were
1
confirmed by elemental analysis, UV-VIS absorption spectra, IR, H NMR,
MS data, and thin layer chromatography. When changing substituents R,
UV-VIS absorption spectra showed bathochromic shift for 2-substituted styryl
benzimidazole dyes 1a–g. The order of bathochromic shift was as follows:
NðCH3Þ2 . OH; OCH3 . CH3; Cl . H; NO2
The absorption maxima (lmax) of a-methyl-2-substituted styryl benzimi-
dazole dyes 2a–f was lower than corresponding 2-substituted styryl
benzimidazole dyes 1a–g.
The IR spectra showed typical aromatic absorption (y55C–H, 3100–
3000 cm21, yC55C, 1650–1400 (s) cm21, d55CH, 700–1000 cm21), resonance
conjugated unsaturated stretching modes in the chromophore (C55C, C55N,
1380–1480 cm21) and the absorption of benzimidazole ring (3388–
1
3447 cm21, 2500–3100 cm21). The H NMR chemical shift data and the
MS m/z values was in accordance with the dye structures.
EXPERIMENTAL
Melting points were taken on a XT-4 micro-melting apparatus and uncor-
rected. TLC analysis was carried out on glass plates coated with silica gel-G,
and spots were visualized using a UV lamp. Elemental analyses were
performed with Vario EL-III instrument. IR spectra in cm21 were recorded
on a Brucker EQUIOX-55 spectrometer. MS were taken on a HP5989B

ORDER
REPRINTS
2248
Wang et al.
instrument. 1H NMR spectra were recorded at 400 MHz on a Varian INOVA-
400 spectrometer and chemical shifts were reported relative to internal Me4Si.
The UV absorption spectra were recorded on a General TU-1201 UV-VIS
spectrometer.
General Procedure for the Synthesis of Dyes
The condensation of 2-alkylbenzimidazole with various aromatic alde-
hydes is carried out in a Galanz microwave oven. 10 mmol 2-methylbenzimi-
dazole or 2-ethylbenzimidazole, 12 mmol aromatic aldehydes and a few drops
of Ac2O were mixed together at ambient temperature in a glass conical flask
(100 mL). The mixture was subjected to microwave irradiation for an opti-
mized time and power. After cooling, 10 mL of 2% kalium hydroxide solution
was added and the crude product was obtained, which was re-crystallized from
the mixture solvent of EtOH-H2O to afford pure dyes. The details of reaction
conditions and yields are provided in Table 1.
Spectral Data of Dyes 1a–2f
1
1a. Yellow solid, mp 206–2078C, H NMR (CDCl3, 400 MHz): d 3.81
(s, 3H, OCH3), 6.84 (d, 2H, J ¼ 8.0 Hz, Ar-H), 7.42 (d, 2H, J ¼ 8.0 Hz,
Ar-H), 6.98 (d, 1H, J ¼ 16.0 Hz, CH55CH), 7.67 (d, 1H, J ¼ 16.0 Hz,
CH55CH), 7.59–7.61 (m, 2H, Ar-H), 7.24–7.26 (m, 2H, Ar-H). IR (KBr)
y: 3430, 2500–3100, 3061, 2992, 2832, 1640, 1601, 1514, 1420, 1248,
1027, 964, 815, 744. MS: m/z: 250 (Mþ, 32), 249 (M 2 H, 100), 235
(M 2 CH3, 76). UV-VIS (MeOH) lmax
: 343 nm. Anal. calcd for
C16H14N2O: C 76.78, H 5.59, N 11.19; found C 76.69, H 5.57, N 11.06.
1b. Yellow solid, mp 263–2648C, 1H NMR (DMSO-d6, 400 MHz):
d 6.83 (d, 2H, J ¼ 8.0 Hz, Ar-H), 7.50 (d, 2H, J ¼ 8.0 Hz, Ar-H), 6.98
(d, 1H, J ¼ 16.0 Hz, CH55CH), 7.56 (d, 1H, J ¼ 16.0 Hz, CH55CH), 7.03–
7.16 (m, 2H, Ar-H), 7.39–7.46 (m, 2H, Ar-H), 9.85 (s, 1H, OH), 12.52
(s, 1H, NH). IR (KBr) y: 3396, 2500–3100, 3054, 2926, 1640, 1598, 1514,
1424, 1266, 1170, 964, 820, 743. MS: m/z: 236 (Mþ, 50), 235 (M 2 H,
100), 219 (M 2 OH, 8). UV-VIS (MeOH) lmax: 344 nm. Anal. calcd for
C15H12N2O: C 74.21, H 5.08, N 9.36; found C 74.32, H 5.10, N 9.40.
1
1c. Yellow solid, mp 201–2028C, H NMR (CDCl3, 400 MHz): d 7.15
(d, 1H, J ¼ 16.0 Hz, CH55CH), 7.67 (d, 1H, J ¼ 16.0 Hz, CH55CH), 7.33
(d, 2H, J ¼ 8.0 Hz, Ar-H), 7.49 (d, 2H, J ¼ 8.0 Hz, Ar-H), 7.33 (d, 2H,
J ¼ 8.0 Hz, Ar-H), 7.61–7.63 (m, 2H, Ar-H), 7.26–7.31 (m, 1H, Ar-H). IR
(KBr) y: 3447, 2500–3100, 3056, 1643, 1586, 1527, 1426, 967, 743, 692.

ORDER
REPRINTS
Synthesis of Styryl Dyes with Benzimidazole Nucleus
2249
MS: m/z: 220 (Mþ, 50), 219 (M 2 H, 100), 218 (M 2 2H, 12). UV-VIS
(MeOH) lmax: 333 nm. Anal. calcd for C15H12N2: C 81.82, H 5.45, N
12.73; found C 81.73, H 5.42, N 12.70.
1
1d. Yellow solid, mp 228–2298C, H NMR (CDCl3, 400 MHz): d 7.09
(d, 1H, J ¼ 16.0 Hz, CH55CH), 7.61 (d, 1H, J ¼ 16.0 Hz, CH55CH), 7.34
(d, 2H, J ¼ 8.0 Hz, Ar-H), 7.45 (d, 2H, J ¼ 8.0 Hz, Ar-H), 7.27–7.30
(m, 2H, Ar-H), 7.60–7.63 (m, 2H, Ar-H). IR (KBr) y: 3445, 2500–3100,
3065, 1640, 1590, 1520, 1489, 1419, 1094, 969, 809, 737. MS: m/z: 254
(Mþ, 49), 256 (M þ 2, 16), 253 (M 2 H, 100), 255 (M þ 2 2 H, 33), 218
(M-Cl, 19). UV-VIS (MeOH) lmax: 338 nm. Anal. calcd for C15H11N2Cl:
C 70.73, H 4.35, N 10.99; found C 70.78, H 4.40, N 10.78.
1
1e. Yellow solid, mp 218–2208C, H NMR (CDCl3, 400 MHz): d 2.33
(s, 3H, CH3), 7.11–7.66 (m, 10H, Ar-H, CH55CH). IR (KBr) y: 3441,
2500–3100, 3041, 2978, 2847, 1640, 1518, 1524, 1422, 962, 802, 740. MS:
m/z: 234 (Mþ, 76), 233 (M 2 H, 100), 218 (M 2 CH4, 16). UV-VIS
(MeOH) lmax: 337 nm. Anal. calcd for C16H14N2: C 82.05, H 5.98, N 11.96;
found C 81.88, H 5.96, N 11.77.
1
1f. Yellow solid, mp 226–2288C, H NMR (CDCl3, 400 MHz): d 8.39
(s, 1H, Ar-H), 8.18 (d, 1H, J ¼ 8.0 Hz, Ar-H), 7.83 (d, 1H, J ¼ 8.0 Hz,
Ar-H), 7.72–7.23 (m, 7H, Ar-H, CH55CH). IR (KBr) y: 3416, 2500–3100,
3073, 1646, 1583, 1526, 1425, 1351, 964, 857, 800, 740. MS: m/z: 265
(Mþ, 46), 264 (M 2 H, 100), 218 (M 2 H 2 NO2, 67), 217 (M 2 2H 2 NO2,
28). UV-VIS (MeOH) lmax: 332 nm. Anal. calcd for C15H11N3O2: C 67.92,
H 4.15, N 15.20; found C 67.89, H 4.15, N 15.07.
1
1g. Brown yellow solid, mp 199–2018C, H NMR (CDCl3, 400 MHz):
d 3.06 (s, 6H, N(CH3)2), 6.44–7.52 (m, 10H, Ar-H, CH55CH). IR (KBr) y:
3412, 2500–3100, 3030, 2920, 1602, 1523, 1446, 946, 810, 741. MS:
m/z: 263 (Mþ, 50), 262 (M 2 H, 100), 219 (M 2 N(CH3)2, 8), 218
(M 2 H 2 N(CH3)2, 8). UV-VIS (MeOH) lmax: 371 nm. Anal. calcd for
C17H17N3: C 76.56, H 6.46, N 14.69; found C 75.91, H 6.29, N 14.38.
1
2a. Yellow solid, mp 198–2008C, H NMR (CDCl3, 400 MHz): d 2.47
(s, 3H, CH3), 3.84 (s, 3H, OCH3), 6.92 (d, 1H, J ¼ 8.0 Hz, Ar-H), 7.20
(d, 2H, J ¼ 8.0 Hz, Ar-H), 7.32 (d, 2H, J ¼ 8.0 Hz, Ar-H), 7.39 (d, 1H,
J ¼ 8.0 Hz, Ar-H), 7.48 (s, 1H, 55CH–), 7.62 (b, 2H, Ar-H). IR (KBr):
3425, 2500–3100, 3054, 2963, 1694, 1603, 1512, 1413, 1446, 1251, 1030,
955, 804, 742. MS: m/z: 264 (Mþ, 12), 263 (M 2 H, 46), 248 (M 2 CH4,
54), 247 (M 2 H 2 CH4, 100), 233 (M 2 OCH3, 18), 232 (M 2 H 2 OCH3,
16). UV-VIS (MeOH) lmax: 316 nm. Anal. calcd for C17H16N2O: C 77.27,
H 6.06, N 10.61; found C 77.56, H 6.03, N 10.48.
2b. Yellow solid, mp 222–2248C, 1H NMR (DMSO-d6, 400 MHz):
d 2.55 (s, 3H, CH3), 6.86 (d, 2H, J ¼ 8.0 Hz, Ar-H), 7.15–7.30 (m, 2H,
A-rH), 7.37 (d, 2H, J ¼ 8.0 Hz, Ar-H), 7.48 (s, 1H, 55CH-), 7.54–7.58

ORDER
REPRINTS
2250
Wang et al.
(m, 2H, Ar-H), 9.74 (s, 1H, OH). IR (KBr): 3388, 2500–3100, 3056, 2967,
1685, 1596, 1507, 1417, 1446, 1276, 1196, 912, 830, 743. MS: m/z:
250 (Mþ, 20), 249 (M 2 H, 100), 247 (M 2 2H, 14), 235 (M 2 CH3, 8).
UV-VIS (MeOH) lmax: 314 nm. Anal. calcd for C16H14N2O: C 76.80,
H 5.60, N 11.20; found C 76.92, H 5.52, N 11.07.
1
2c. Yellow solid, mp 242–2448C, H NMR (CDCl3, 400 MHz): d 2.48
(s, 3H, CH3), 7.26–7.41 (m, 7H, Ar-H), 7.54 (s, 1H, 55CH–), 7.63–7.64
(m, 2H, Ar-H). IR (KBr): 3426, 2500–3100, 3061, 2968, 1625, 1592, 1521,
1488, 1447, 1418, 955, 748, 698. m/z: 234 (Mþ, 81), 233 (M 2 H, 100),
235 (M þ H, 11), 219 (M 2 CH3, 26), 218 (M 2 CH4, 22). UV-VIS
(MeOH) lmax: 311 nm. Anal. calcd for C16H14N2: C 82.02, H 6.02, N 11.95;
found C 82.01, H 6.02, N 11.93.
1
2d. Yellow solid, mp 249–2518C, H NMR (CDCl3, 400 MHz): d 2.46
(s, 3H, CH3), 7.26–7.36 (m, 6H, Ar-H), 7.50 (s, 1H, 55CH–), 7.64 (s, 2H,
Ar-H). IR (KBr): 3427, 2500–3100, 3057, 2967, 1622, 1590, 1521, 1488,
1420, 1446, 1095, 956, 825. m/z: 268 (Mþ, 50), 270 (M þ 2, 17), 267
(M 2 H, 100), 269 (M þ 2 2 H, 32). UV-VIS (MeOH) lmax: 320 nm. Anal.
calcd for C16H13N2Cl: C 71.51, H 4.87, N 10.42; found C 71.48, H 4.85,
N 10.45.
2e. Yellow solid, mp 178–1808C, 1H NMR (CDCl3, 400 MHz): d 2.37–
2.48 (m, 6H, 2CH3), 7.19 (d, 2H, J ¼ 8.0 Hz, Ar-H), 7.29 (d, 2H, J ¼ 8.0 Hz,
Ar-H), 7.11–7.27 (m, 2H, Ar-H), 7.48 (s, 1H, 55CH–), 7.61–7.62 (m, 2H,
Ar-H). IR (KBr): 3425, 2500–3100, 3052, 2966, 1630, 1519, 1446, 1416,
954, 802, 741. m/z: 248 (Mþ, 19), 247 (M 2 H, 100), 233 (M 2 CH3, 3).
UV-VIS (MeOH) lmax: 316 nm. Anal. calcd for C17H16N2: C 82.22, H 6.49,
N 11.28; found C 82.19, H 6.46, N 11.25.
1
2f. Yellow solid, mp 231–2338C, H NMR (CDCl3, 400 MHz): d 2.51
(s, 3H, CH3), 7.26–7.66 (m, 6H, Ar-H), 7.74 (d, 1H, J ¼ 8.0 Hz, Ar-H),
8.17 (d, 1H, J ¼ 8.0 Hz, Ar-H), 8.28 (s, 1H, 55CH–). IR (KBr): 3424,
2500–3100, 3062, 2968, 1617, 1526, 1477, 1446, 1416, 1353, 965, 743.
m/z: 279 (Mþ, 24), 278 (M 2 H, 100), 233 (M 2 NO2, 18). UV-VIS
(MeOH) lmax: 312 nm. Anal. calcd for C16H13N3O2: C 68.80, H 4.69,
N 15.04; found C 68.77, H 4.68, N 15.06.
CONCLUSIONS
We have described a rapid and highly efficient method for the synthesis
of styryl dyes with benzimidazole nucleus through the condensation of
2-methylbenzimidazole or 2-ethylbenzimidazole with aromatic aldehydes in
the presence of Ac2O under solvent-free microwave irradiation conditions.

ORDER
REPRINTS
Synthesis of Styryl Dyes with Benzimidazole Nucleus
2251
The procedure offers several advantages including short reaction times, cleaner
reaction profiles, and simple experimental/product isolation procedures.
ACKNOWLEDGMENTS
We appreciate the financial support for this research by a grant from the
Special Science Research Foundation of Education Committee of Shaanxi
Province (No. 02JK060).
REFERENCES
1. Mees, C.E.K.; James, T. The Theory of the Photographic Process, Part 1;
Science Press: Beijing, 1979; H. Tao Trans.
2. Hamer, F.M. The Cyanine Dyes and Related Compound; Interscience
Publishers: New York, 1964; 398.
3. Pierre, G. Photographic Chemistry, Part 4; Chinese Film Press: Beijing,
1984; D. Liu Trans.
4. Li, Q.; Lin, G.L.; Peng, B.X.; Li, Z.X. Synthesis, characterization and
photographic properties of some new styryl cyanine dyes. Dyes Pigments
1997, 38, 211.
5. Preston, P.N. Commercial applications of benzimidazoles. In Benzimida-
zoles and Congeneric Tricyclic Compounds, Part 2; John Wiley:
New York, 1980; Chap. 10, 531.
6. Guo, Z.X.; Hao, J.X.; Zhang, Z.X.; Cao, Z.X. The covalent binding of
photosensitive dyes to monocrystalline silicon surface and their spectral
response. Sci. China B 1993, 36, 1416 (Chinese).
7. Zhang, Z.J.; Hao, J.X.; Wu, B.Y.; Yuan, H.A. Thermodynamics of a blue-
sensitizing cyanine dye in aqueous methanol solution. J. Imaging Sci.
Techn. 1995, 39, 373.
8. Zhang, Z.X.; Zhang, Y.J.; Hao, J.X.; Zhang, Z.J.; Li, C.E. Synthesis of a
new silacarbocyanine dye and its application in silver bromide emulsion.
Sci. China B 1995, 38, 1173 (Chinese).
9. Zhang, C.L.; Wang, L.Y.; Zhang, X.H.; Zhang, Z.X.; Cao, Z.X. Studies of
photosensitive dyes binding to monocrystalline germanium surface.
J. Funct. Mater. 2001, 32, 546 (Chinese).
10. Tjjen, O.; Bilge, C.; Ufuk, A.; Feth, S.M. 2-Styrylbenzimidazole deriva-
tives synthesis and antimicrobial activities. J. Fac. Pham. Qazi. Univ.
1995, 12, 29.

ORDER
REPRINTS
2252
Wang et al.
11. Ramaiah, K.; Dubey, P.K.; Rao, D.E.; Ramesh, K.; Grossert, J.;
Hooper, D.L. Synthesis and spectral properties of a variety of 2-styrylben-
zimidazoles. Indian J. Chem. Sect. B. 2000, 39, 904.
¨
12. Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Microwave assisted
organic synthesis—a review. Tetrahedron 2001, 57, 9225.
13. Yadav, J.S.; Reddy, B.V.S. Microwave-assisted rapid synthesis of the
cytotoxic alkaloid luotonin A. Tetrahedron Lett. 2002, 43, 1905.
Received in Japan December 15, 2003

Request Permission or Order Reprints Instantly!
Interested in copying and sharing this article? In most cases, U.S. Copyright
Law requires that you get permission from the article’s rightsholder before
using copyrighted content.
All information and materials found in this article, including but not limited
to text, trademarks, patents, logos, graphics and images (the "Materials"), are
the copyrighted works and other forms of intellectual property of Marcel
Dekker, Inc., or its licensors. All rights not expressly granted are reserved.
Get permission to lawfully reproduce and distribute the Materials or order
reprints quickly and painlessly. Simply click on the "Request Permission/
Order Reprints" link below and follow the instructions. Visit the
U.S. Copyright Office for information on Fair Use limitations of U.S.
copyright law. Please refer to The Association of American Publishers’
Fair Use in the Classroom.
(AAP) website for guidelines on
The Materials are for your personal use only and cannot be reformatted,
reposted, resold or distributed by electronic means or otherwise without
permission from Marcel Dekker, Inc. Marcel Dekker, Inc. grants you the
limited right to display the Materials only on your personal computer or
personal wireless device, and to copy and download single copies of such
Materials provided that any copyright, trademark or other notice appearing
on such Materials is also retained by, displayed, copied or downloaded as
part of the Materials and is not removed or obscured, and provided you do
not edit, modify, alter or enhance the Materials. Please refer to our
Website
User Agreement for more details.
Request Permission/Order Reprints
Reprints of this article can also be ordered at
http://www.dekker.com/servlet/product/DOI/101081SCC120038508