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In terms of energy per pound it's easily smokeless powder. No question.
Single based powders are nitrocellulose (gun cotton), double based powders are nitrocellulose dissolved in nitroglycerin.
Black powder is an explosive (creates gas very rapidly!), smokeless powder is a propellant (converted into mostly gas, is consumed more), so black powder is better suited to putting a hole in the ground.
The key to smokeless powder is it's controllable burn rate and ability to efficiently convert itself to gas. Where as black powders burn rate can only be roughly controlled by the size of the grains and doesn't produces nearly the same volume of gas. In fact, you get a lot of fouling, better off converting your solid into gas if you want to propel a bullet instead of fouling.
That's my understand of it, anyway.
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