Make the cupcakes: Heat oven to 350° F. Line a standard 12-cup muffin tin with paper liners. Whisk together the flour, sugar, cocoa, baking soda, baking powder, and salt in a medium bowl; set aside.
In a separate bowl, whisk together the soy milk and vinegar; set aside until curdled, 5 minutes. Whisk in the canola oil and vanilla extract.
Whisk the wet ingredients into the dry ingredients until just combined (do not overmix). Divide the batter among the muffin cups and bake until a toothpick inserted in the center comes out clean, 15 to 18 minutes. Let cool in the tin for 5 minutes, then transfer to a wire rack to cool completely.
Make the frosting: Place the chopped chocolate in a small bowl. Heat the soy milk in a small pot over medium heat. Pour over the chocolate (make sure all the chocolate is covered). Let sit for 2 minutes, then whisk until smooth and shiny. Let cool for 5 minutes. Frost the cupcakes and top each with a raspberry.