Optically active tetraazamacrocycles analogous to cyclam |
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| Affiliation: | 1. Baku State University, AZ-1148 Baku, Azerbaijan;2. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;3. St. Petersburg State University, 199034 St. Petersburg, Russian Federation;4. Peoples Friendship University of Russia (RUDN University), 117198 Moscow, Russian Federation;5. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation;6. N. N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, 119991 Moscow, Russian Federation;1. School of Engineering and Applied Sciences, Nile University, Giza 12588, Egypt;2. Department of Mathematics, Faculty of Science, Cairo University, Giza 12613, Egypt;1. National Institute of Clean-and-Low-Carbon Energy, Beijing 102211, China;2. State Key Laboratory of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China;1. Department of Polymer Science and Rubber Technology, Cochin University of Science and Technology, Cochin-22, India;2. Department of Physics, Cochin University of Science and Technology, Cochin-22, India;3. School of Chemical Sciences, Mahatma Gandhi University, Kottyam, 686 560, India;4. Department of Applied Chemistry, Cochin University of Science and Technology, Cochin-22, India;1. WiscSIMS, Department of Geoscience, University of Wisconsin-Madison, 1215 W. Dayton St., Madison, WI 53706, USA;2. Kochi Institute for Core Sample Research, Japan Agency for Marine-Earth Science and Technology (JAMSTEC), 200 Monobe-otsu, Nankoku, Kochi 783-8502, Japan;3. Chemistry Division, Nuclear and Radiochemistry, Los Alamos National Laboratory, MSJ514, Los Alamos, NM 87545, USA;4. Department of Earth and Planetary Science, Graduate school of Science, University of Tokyo, 7-3-1 Hongo, Bunkyo, Tokyo 113-0033, Japan |
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| Abstract: | The syntheses of enantiopure tetraazamacrocycles analogous to cyclam, (S,S)-3, (R,R)-3 and (S,S,S,S)-4, have been carried out. NMR and semiempirical studies of 3 have revealed that this compound presents a rigid conformation with C2 symmetry, which is stabilized by intramolecular bifurcated hydrogen bonds. Structural studies for macrocycle 4 have shown that the presence of two cyclohexane rings of (S,S) configuration leads to the loss of the D2 symmetry in solution, which is in agreement with the AM1 calculated structure. |
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